N-azinyl-N&#39;-(het) arylsulphonyl-ureas

ABSTRACT

The invention relates to novel (het)arylsulphonyl compounds of the formula 
     
         J--SO.sub.2 --G 
    
     wherein 
     G is --NH 2 , N═C═O or --NH--COOR 12   
     wherein 
     R 12  is alkyl or aryl, and 
     J is a member selected form the group consisting of ##STR1##

This application is a divisional of application Ser. No. 08/696,709,filed on Aug. 14, 1996, now U.S. Pat. No. 5,696,257, which is a divisionof Ser. No. 08/528,452, filed on Sep. 14, 1995, now U.S. Pat. No.5,580,842, which is a division of 08/309,292, filed on Sep. 20, 1994,now U.S. Pat. No. 5,476,936.

The invention relates to novel N-azinyl-N'-(het)arylsulphonyl-ureas, toprocesses and novel intermediates for their preparation, and to theiruse as herbicides.

It is already known that certain N-azinyl-N'-arylsulphonylureas havingsimple open-chain hydroxamic ester groups in the aryl moiety, such as,for example,N-(4,6-dimethylpyrimidin-2-yl)-N'-(2-methoxylaminocarbonyl-phenylsulphonyl)-ureaand the corresponding-N'-(2-n-octyloxyaminocarbonylphenylsulphonyl)-urea, exhibit herbicidalproperties (cf. DE-A-3 516 435; EP-A-173 958; U.S. Pat. No. 4,704,158).However, the herbicidal effect of these known compounds is notsatisfactory in all respects.

In addition, certain herbicidally-activeN-azinyl-N'-(het)arylsulphonyl-ureas have also become well known whichare substituted in the (het)aryl moiety by O,O-dialkylated, likewiseopen-chain hydroxamic acid groups (cf. EP-A-301 784); by contrast,corresponding cyclic hydroxamic acid derivatives have not hitherto beendescribed.

Novel N-azinyl-N'-(het)arylsulphonyl-ureas of the general formula (I)##STR2## have now been found in which A represents nitrogen or a CR¹¹group,

where

R¹¹ represents hydrogen, alkyl, halogen and haloalkyl,

R¹ represents hydrogen or an optionally substituted radical from theseries alkyl, alkoxy, alkoxyalkyl, alkenyl, alkinyl, cycloalkyl,cycloalkylalkyl, aralkyl and aryl,

R² represents hydrogen or halogen, or represents alkyl, alkoxy,alkythio, alkylamino or dialkylamino having in each case 1 to 6 carbonatoms which are in each case optionally substituted by halogen,

R³ represents hydrogen or halogen, or represents alkyl, alkoxy,alkylthio, alkylamino or dialkylamino having in each case 1 to 6 carbonatoms which are in each case optionally substituted by halogen,

J represents J-1 to J-4, where J-1 to J-4 have the following meanings:##STR3## in which E represents a direct linkage, alkylene, oxygen,alkylamino or sulphur,

R⁴ -R⁷, independently of each other, represent hydrogen, halogen, cyanoor thiocyanato, or represent alkyl, alkoxy, alkylthio, alkylsulphinyl,alkylsulphonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl oralkylaminocarbonyl having in each case 1 to 3 carbon atoms which are ineach case optionally substituted by halogen,

R⁸ represents hydrogen or an optionally substituted radical from theseries alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aralkyl andaryl, or represents a group C(═O)R⁹,

where

R⁹ represents hydrogen, optionally substituted alkyl, optionallysubstituted aryl, alkoxy, alkylamino or dialkylamino,

R¹⁰ represents hydrogen, halogen, cyano or thiocyanato, or representsalkyl, alkoxy, aikylthio, alkylsulphinyl, alkylsulphonyl, alkylamino,alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl having in each case1 to 3 carbon atoms which are in each case optionally substituted byhalogen,

where, in the abovementioned radicals, the alkyl and alkylene groups canin each case contain 1 to 6 C atoms, the alkenyl and alkinyl groups ineach case 2 to 6 C atoms, the cycloalkyl groups in each case 3 to 6 Catoms and the aryl groups in each case 6 or 10 C atoms,

as well as salts of compounds of the formula (I).

Accordingly, the (5,6-dihydro- 1,4,2!-dioxazin-3-yl) radical, as anovel, heterocyclic substituent in the (het)aryl moiety of theN-azinyl-N'-(het)arylsulphonyl-ureas, is a characteristic structuralfeature of the novel sulphonylureas (I). The simple parent substance,which is not further substituted, of this compound class--(5,6-dihydro-1,4,2!-dioxazin-3-yl)benzene, which can also be termed3-phenyl-5H-1,4,2-dioxazine--is known (cf. J. E. Johnson et al., J. Org.Chem., Vol. 36 (2), (1971), pp. 284-294).

The novel N-azinyl-N'-(het)arylsulphonyl-ureas of the general formula(I) are obtained when

(a) (het)arylsulphonamides of the general formula (II),

    J--SO.sub.2 --NH.sub.2                                     (II),

in which

J has the abovementioned meanings,

are reacted with N-azinyl carbamates of the formula (III), ##STR4## inwhich A and R¹ -R³ have the abovementioned meanings, and

R¹² represents alkyl or aryl,

optionally in the presence of a diluent and optionally in the presenceof a reaction auxiliary, or when

(b) (het)arylsulphonyl isocyanates of the general formula (IV),

    J--SO.sub.2 --NCO                                          (IV)

in which

J has the abovementioned meanings,

are reacted with aminoazines of the formula (V), ##STR5## in which A andR¹ -R³ have the abovementioned meanings,

optionally in the presence of a diluent and optionally in the presenceof a reaction auxiliary, or when

(c) N-(het)arylsulphonyl carbamates of the general formula (VI),##STR6## in which J and R¹² have the abovementioned meanings,

are reacted with aminoazines of the formula (V), ##STR7## in which A andR¹ -R³ have the abovementioned meanings,

optionally in the presence of a diluent and optionally in the presenceof a reaction auxiliary,

and the products obtained by processes (a), (b) or (c) are optionallyconverted into salts in accordance with customary methods.

The novel N-azinyl-N'-(het)arylsulphonyl-ureas of the formula (I) arenotable for strong herbicidal activity.

Surprisingly, the novel compounds of the formula (I) exhibit aconsiderably stronger effect than do the compoundsN-(4,6-dimethylpyrimidin-2-yl)-N'-(2-methoxyaminocarbonyl-phenylsulphonyl)-ureaand the corresponding-N'-(2-n-octyloxyaminocarbonyl-phenylsulphonyl)-urea, which arecomparable from the point of view of structure and profile of activity.

The invention preferably relates to compounds of the formula (I)

in which

A represents nitrogen or a CH group,

R¹ represents hydrogen or a radical from the series alkyl, alkoxy,alkoxyalkyl, alkenyl and alkinyl having in each case up to 3 carbonatoms which is optionally substituted by halogen,

R² represents hydrogen or halogen, or represents alkyl, alkoxy,alkylthio, alkylamino or dialkylamino having in each case 1 to 3 carbonatoms in the alkyl radicals and which are in each case optionallysubstituted by halogen,

R³ represents hydrogen or halogen, or represents alkyl, alkoxy,alkylthio, alkylamino or dialkylamino having in each case 1 to 3 carbonatoms in the alkyl radicals and which are in each case optionallysubstituted by halogen,

J represents J-1 to J-4,

E represents a direct linkage, methylene, oxygen, alkylamino having 1 to3 carbon atoms, or sulphur,

R⁴ -R⁷, independently of each other, represent hydrogen, halogen, cyanoor thiocyanato, or represent alkyl, alkoxy, alkylthio, alkylsulphinyl,alkylsulphonyl, alkylamino, alkylcarbonyl, alkoxycarbonyl oralkylaminocarbonyl having in each case 1 to 3 carbon atoms in the alkylradicals and which are in each case optionally substituted by halogen,

R⁸ represents hydrogen or an optionally substituted radical from theseries C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₇ -C₁₁ -aralkyl and C₆ -C₁₀-aryl,

R¹⁰ represents hydrogen, halogen, cyano or thiocyanato, or representsalkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino,alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl having in each case1 to 3 carbon atoms in the alkyl radicals and which are in each caseoptionally substituted by halogen.

The invention further relates preferably to salts which are obtained bycustomary processes from compounds of the formula (I) and bases, suchas, for example, sodium, potassium or calcium hydroxide, hydride, amideand carbonate, sodium or potassium C₁ -C₄ -alkanolates, ammonia, C₁ -C₄-alkylamines, di-(C₁ -C₄ -alkyl)-amines or tri-(C₁ -C₄ -alkyl)-amines.

The invention relates, in particular, to compounds of the formula (I),

in which

A represents nitrogen or a CH group,

R¹ represents hydrogen, methyl, ethyl, methoxy, methoxymethyl or ethoxy,

R² represents hydrogen, chlorine, methyl, ethyl, tri fluoromethyl,methoxy, ethoxy, difluoromethoxy, methylthio, methylamino ordimethylamino,

R³ represents hydrogen, chlorine, methyl, ethyl, tri-fluoromethyl,methoxy, ethoxy, difluoromethoxy, methylthio, methylamino ordimethylamino,

J represents J-1 to J-4,

E represents a direct linkage, methylene, oxygen, C₁ -C₂ -alkylamino orsulphur,

R⁴ -R⁷, independently of each other, represent hydrogen, fluorine,chlorine or cyano, or represent methyl, methylthio, methylsulphinyl,methylsulphonyl, methoxycarbonyl and ethoxycarbonyl which are in eachcase optionally substituted by chlorine or fluorine,

R⁸ represents hydrogen, methyl, ethyl, phenyl or benzyl,

R¹⁰ represents hydrogen, fluorine, chlorine, bromine or cyano, orrepresents methyl, methoxy, ethoxy, methylthio, ethylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl,methylamino or dimethylamino which are in each case optionallysubstituted by chlorine or fluorine.

The above-listed general radical definitions, or those radicaldefinitions listed in preference ranges, apply both to the end productsof the formula (I) and also, in a corresponding manner, to the startingcompounds or intermediates which are in each case required for thepreparation. These radical definitions can be combined arbitrarily amongthemselves, that is also between the given preferred ranges.

The hydrocarbon radicals mentioned in the radical definitions, such asalkyl, alkenyl or alkinyl, also when in combinations with heteroatoms,such as in alkoxy, alkylthio or alkylamino, are straight-chain orbranched, even when this is not expressly indicated.

If, for example, 2-(5,6-dihydro-1,4,2!-dioxazin-3-yl)benzenesulphonamide and(4,6-dimethoxypyrimidin-2-yl)-phenyl carbamate are used as startingcompounds for process variant (a), the course of the reaction can thenbe outlined by the following formula scheme: ##STR8## If, for example,2-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)benzenesulphonyl isocyanate and2-amino-4,6-dimethoxypyrimidine are used as starting compounds forprocess variant (b), the course of the reaction can then be outlined bythe following formula scheme: ##STR9## If, for example,N-(2-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)benzenesulphonyl)-phenylcarbamate and 2-amino-4,6-dimeth-oxypyrimidine are used as startingcompounds for process variant (c), the course of the reaction can thenbe outlined by the following formula scheme: ##STR10##

The (het)arylsulphonamides which are to be used as starting compoundsfor preparing compounds of the formula (I) in process (a) according tothe invention are defined generally by formula (II). In formula (II), Jpreferably or in particular has those meanings which have already beenindicated above, in connection with the description of the compounds ofthe formula (I) according to the invention, as being preferred orparticularly preferred for J.

The following may be mentioned as examples of the compounds of theformula (II):

2-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)benzenesulphonamide,2-(5,6-dihydro-1,4,2!-dioxazin-3-yl)-6-methyl-benzenesulphonamide2-(5,6-dihydro-1,4,2!-dioxazin-3-yl)-phenylmethanesulphonamide, 3-(5,6-dihydro-1,4,2!-dioxazin-3-yl)pyridine-2-sulphonamide, 2-(5,6-dihydro-1,4,2!-dioxazin-3-yl)thiophene-3-sulphonamide, 1-methyl-4-(5,6-dihydro-1,4,2!-dioxazin-3-yl)pyrazole-5-sulphonamide, and1-methyl-3-chloro-4-(5,6-dihydro-1,4,2!-dioxazin-3-yl)pyrazole-5-sulphonamide.

The starting compounds of the formula (II) are still not known from theliterature and, as novel compounds, are also a subject of the presentinvention.

Processes for preparing the compounds of the formula (II) are describedfurther below cf. processes (d) and (e)!.

The N-azinyl carbamates which are also to be used as starting compoundsin process (a) are defined generally by formula (III). In formula (III),A, R¹, R² and R³ preferably or in particular have those meanings whichhave already been indicated above, in connection with the description ofthe compounds of formula (I) according to the invention, as beingpreferred or particularly preferred for A, R¹, R² and R³. R¹² preferablyrepresents C₁ -C₆ -alkyl or C₆ -C₁₀ -aryl, and particularly preferablyrepresents C₁ -C₄ -alkyl or phenyl.

The following may be mentioned as examples of intermediates of theformula (III):

N-(4,6-dimethoxypyrimidin-2-yl)-phenyl carbamate,N-(4,6-diethoxypyrimidin-2-yl)-phenyl carbamate,N-methyl-N-(4,6-dimethoxypyrimidin-2-yl)-phenyl carbamate,N-methoxymethyl-N-(4,6-dimethoxypyrimidin-2-yl)-phenyl carbamate,N-(4,6-dimethylpyrimidin-2-yl)-phenyl carbamate,N-(4,6-dimethylpyrimidin-2-yl)-phenyl carbamate, N-4,6-bis(difluormethoxy)pyrimidin-2-yl!-phenyl carbamate, N-4,6-bis(dimethylamino)pyrimidin-2-yl!-phenyl carbamate,N-(4-methyl-6-ethylpyrimidin-2-yl)-phenyl carbamate,N-(4-methoxy-6-chlorpyrimidin-2-yl)-phenyl carbamate,N-(4-ethoxy-6-methylaminotriazin-2-yl)-phenyl carbamate,N-(4-methoxy-6-methyltriazin-2-yl)-phenyl carbamate,N-(4-isopropoxy-6-chlortriazin-2-yl)-phenyl carbamate,N-(4-methoxy-6-chlortriazin-2-yl)-phenyl carbamate, N-4-(2,2,2-trifluoroethoxy)-6-dimethylaminotriazin-2-yl!-phenylcarbamate,N-(4-trifluoromethyl-6-methoxytriazin-2-yl)-phenyl carbamate,N-(4-methylamino-6-chlortriazin-2-yl)-phenyl carbamate,N-(4-methoxy-6-dimethylaminotriazin-2-yl)-phenyl carbamate,N-(4,6-dimethoxytrazin-2-yl)-phenyl carbamate,N-(4,6-diethoxytriazin-2-yl)-phenyl carbamate,N-(4,6-dimethyltriazin-2-yl)-phenyl carbamate,N-(4-methyl-6-chlorpyrimidin-2-yl)-phenyl carbamate,N-(4-methoxy-6-methylpyrimidin-2-yl)-phenyl carbamate,N-(4-methoxy-6-ethoxypyrimidin-2-yl)-phenyl carbamate,N-(4-methoxy-6-dimethylaminopyrimidin-2-yl)-phenyl carbamate,N-(4-ethoxy-6-chlorpyrimidin-2-yl)-phenylcarbamate,N-(4-ethoxy-6-dimethylaminopyrimidin-2-yl)-phenylcarbamate,N-(4-methyl-6-dimethylaminopyrimidin-2-yl)-phenyl carbamate,N-(4-methyl-6-isopropoxypyrimidin-2-yl)-phenyl carbamate,N-(4-dimethylamino-6-chlorpyrimidin-2-yl)-phenyl carbamate,N-(4-methylamino-6-chlorpyrimidin-2-yl)-phenyl carbamate,N-(4-difluoromethoxy-6-methylpyrimidin-2-yl)-phenyl carbamate, N-4-(2,2,2-trifluoroethoxy)-6-methylpyrimidin-2-yl!-phenyl carbamate, N-4-(2,2,2-trifluoroethoxy)-6-chlorpyrimidin-2-yl!-phenyl carbamate.

The starting compounds of the formula (III) are known and/or can beprepared by processes which are known per se (cf. EP-238 070).

The (het)arylsulphonyl isocyanates to be used as starting compounds forpreparing compounds of the formula (I) in process (b) according to theinvention are defined generally by formula (IV). In formula (IV), Jpreferably or in particular has those meanings which have already beenindicated above, in connection with the description of the compounds ofthe formula (I) according to the invention, as being preferred orparticularly preferred for J.

The following may be mentioned as examples of the starting compounds ofthe formula (IV):

2-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)benzenesulphonyl isocyanate,2-(5,6-dihydro-1,4,2!-dioxazin-3-yl)-6-methyl-benzenesulphonylisocyanate,2-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)phenylmethanesulphonyl isocyanate,3-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)-pyridine-2-sulphonylisocyanate,2-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)thiophene-3-sulphonyl isocyanate,1-methyl-4-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)-pyrazole-5-sulphonylisocyanate, and 1-methyl-3-chloro-4-(5,6-dihydro-1,4,2!-dioxazin-3-yl)-pyrazole-5-sulphonyl isocyanate.

The starting compounds of the formula (IV) are still not known from theliterature and, as novel compounds, are also a subject of the presentinvention.

The novel (het)arylsulphonyl isocyanates of the formula (IV) areobtained by reacting (het)arylsulphonamides of the above formula (II)with phosgene in the presence of a diluent, such as, for example,chlorobenzene, and of reaction auxiliaries, such as, for example, butylisocyanate and diazabicyclooctane (DABCO), at temperatures of between 0°C. and 200° C., preferably of between 20° C. and 160° C., andsubsequently carefully distilling off the volatile components underreduced pressure (cf. EP-162 723).

The aminoazines which are further required as starting compounds forpreparing compounds of the formula (I) in process (b) according to theinvention are defined generally by formula (V). In formula (V), A, R¹,R² and R³ preferably or in particular have those meanings which havealready been indicated above, in connection with the description of thecompounds of the formula (I) according to the invention, as beingpreferred or particularly preferred for A, R¹, R² and R³.

The following may be mentioned as examples of the starting compounds ofthe formula (V):

2-amino-4,6-dimethoxypyrimidine, 2-amino-4,6-diethoxypyrimidine,2-methylamino-4,6-dimethoxypyrimidine,2-methoxymethylamino4,6-dimethoxypyrimidine,2-amino-4,6-dimethylpyrimidine, 2-amino-4,6-diethylpyrimidine,2-amino-4,6-bis(difluormethoxy)pyrimidine,2-amino-4,6-bis(dimethylamino)pyrimidine,2-amino-4-methyl-6-ethylpyrimidine,2-amino-4-methoxy-6-chlorpyrimidine,2-amino-4-ethoxy-6-methylaminotriazine,2-amino-4-methoxy-6-methyltriazine,2-amino-4-isopropoxy-6-chlortriazine, 2-amino-4-methoxy-6-chlortriazine,2-amino-4-(2,2,2-trifluorethoxy)-6-dimethylaminotriazine,2-amino-4-trifluormethyl-6-methoxytriazine,2-amino-4-methylamino-6-chlortriazine,2-amino-4-methoxy-6-dimethylaminotriazine,2-amino-4,6-dimethoxytriazine, 2-amino-4,6-diethoxytriazine,2-amino-4,6-dimethyltriazine, 2-amino-4-methyl-6-chlorpyrimidine,2-amino-4-methoxy-6-methylpyrimidine,2-amino-4-methoxy-6-ethoxypyrimidine,2-amino-4-methoxy-6-dimethylaminopyrimidine,2-amino-4-ethoxy-6-chlorpyrimidine,2-amino-4-ethoxy-6-dimethylaminopyrimidine,2-amino-4-methyl-6-dimethylaminopyrimidine,2-amino-4-methyl-6-isopropoxypyrimidine,2-amino-4-dimethylamino-6-chlorpyrimidine,2-amino-4-(2,2,2-trifluorethoxy)-6-chlorpyrimidine,2-amino-4-methylamino-6-chlorpyrimidine,2-amino-4-difluormethoxy-6-methylpyrimidine,2-amino-4-(2,2,2-trifluorethoxy)-6-methylpyrimidine.

The starting compounds of the formula (V) are known and/or can beprepared by processes which are known per se (cf. Huaxue Shijie, 32(6),254-7 (1991); JP-01 016 770; EP-246 984); some of these compounds arecommercially obtainable as chemicals for use in syntheses.

The (het)arylsulphonyl carbamates to be used as starting compounds forpreparing compounds of the formula (I) in process (c) according to theinvention are defined generally by formula (VI). In formula (VI), J andR¹² prefer-ably or in particular have those meanings which have alreadybeen indicated above, in connection with the description of thecompounds of the formulae (I) and (III) according to the invention, asbeing preferred or particularly preferred for J and R¹².

The following may be mentioned as examples of the starting compounds ofthe formula (VI).

N-(2-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)benzenesulphonyl)-phenylcarbamate, N-(2-(5,6-dihydro-1,4,2!-dioxazin-3-yl)-6-methyl-benzenesulphonyl)-phenyl carbamate,N-(2-(5,6-di-hydro- 1,4,2!-dioxazin-3-yl)phenylmethanesulphonyl)-phenylcarbamate, N-(3-(5,6-dihydro-1,4,2!-dioxazin-3-yl)pyridine-2-sulphonyl)-phenyl carbamate,N-(2-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)thiophene-3-sulphonyl)-phenylcarbamate, N-(1-methyl-4-(5,6-dihydro-1,4,2!-dioxazin-3-yl)pyrazole-5-sulphonyl)phenyl carbamate, andN-(1-methyl-3-chloro-4-(5,6-dihydro-t1,4,2!-dioxazin-3-yl)pyrazole-5-sulphonyl)-phenyl carbamate.

The starting compounds of the formula (VI) are still not known from theliterature and, as novel compounds, are also a subject of the presentinvention.

The novel (het)arylsulphonyl carbamates of the formula (VI) are obtainedby reacting (het)arylsulphonamides of the above formula (II) withchloroformic esters in the presence of a diluent, such as, for example,dioxane or acetonitrile, and of reaction auxiliaries, such as, forexample, pyridine, potassium carbonate or calcium carbonate, attemperatures of between 0° C. and 120° C., preferably of between 20° C.and 100° C., and subsequently carefully distilling off the volatilecomponents under reduced pressure (cf. JP-04139170).

The aminoazines of the formula (V) which are further required asstarting compounds in process (c) according to the invention havealready been described in more detail above in process (b).

The novel, closely-related, starting compounds and intermediates of theformulae (II), (IV) and (VI), which have been described above, may, insummary, be designated "(het)arylsulphonyl compounds", and representedby the following formula (XI):

    J--SO.sub.2 --G                                            (XI),

in which

J has the meanings mentioned above for formula (I), and

G represents --N═C═O or --NH--COOR¹², where R¹² has the abovementionedmeaning.

It has, furthermore, been found that the abovedescribed(het)arylsulphonamides of the formula (II) are obtained when

(d) (het)arylthiobenzyl ethers of the formula (VII), ##STR11## in whichJ has the meanings mentioned above for formula (I),

is reacted with a chlorinating agent and water in the presence of aninert organic diluent, and optionally of a reaction auxiliary, and thesulphonyl chlorides thus obtained are reacted with ammonia or anammonium salt in the presence of an inert organic diluent, andoptionally of a reaction auxiliary (cf. EP-232 067, EP-451 468, U.S.Pat. No. 5,157,119).

If, for example, 1-benzylthio-2-(5,6-dihydro-1,4,2!-dioxazin-3-yl)-benzene, chlorine, water and ammonia are used asstarting compounds for process (d), the course of the reaction can thenbe outlined by the following reaction scheme: ##STR12## (e)Alternatively, the novel (het)arylsulphonamides of the formula (II) areobtained when (het)arylsulphonamides of the formula (VIII),

    T--SO.sub.2 NH.sub.2                                       (VIII)

in which

T represents T-1 to T-4,

where

T-1 to T4 have the following meanings: ##STR13## in which E, R⁸ and R¹⁰have the abovementioned meanings, and

R¹³ represents alkyl or aryl, and preferably represents C₁ -C₄ -alkyl orphenyl,

are reacted with hydroxylamine hydrochloride and a substituted alkane ofthe formula (IX), ##STR14## in which R⁴ -R⁷ have the abovementionedmeanings, and

X and Y, independently of each other represent halogen, or representalkylcarbonyloxy, arylcarbonyloxy, alkylsulphonyloxy or arylsulphonyloxywhich are optionally substituted (preferably represent chlorine,bromine, iodine, C₁ -C₆ -alkylcarbonyloxy, C₆ -C₁₂ -arylcarbonyloxy, C₁-C₆ -alkylsulphonyloxy or C₆ -C₁₂ -arylsulphonyloxy),

optionally in the presence of an organic diluent and optionally in thepresence of a reaction auxiliary (cf. J. Org. Chem., Vol. 36(2), pp.284-294 (1971); JP-O1 221 371).

If, for example, 1-methyl-4-ethoxycarbonylpyrazole-5-sulphonamide,hydroxylamine hydrochloride and 1,2-dibromoethane are used as startingcompounds for process (e), the course of the reaction can then beoutlined by the following reaction scheme: ##STR15##

The (het)arylthiobenzyl ethers which are required as starting compoundsfor preparing compounds of the formula (II) in process (d) are definedgenerally by formula (VII). In formula (VII), J preferably or inparticular has those meanings which have already been indicated above,in connection with the description of the compounds of the formula (I)according to the invention, as being preferred or particularly preferredfor J.

The following may be mentioned as examples of the intermediates of theformula (VII):

1-benzylthio-2-(5,6-dihydro- 1,2,4!-dioxazin-3-yl)-benzene,1-benzylthio-2-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)-6-methyl-benzene,1-benzylthiomethyl-2-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)-benzene,2-benzylthio-3-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)-pyridine,1-methyl-5-benzylthio-4-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)-pyrazole,1-methyl-3-chloro-5-benzylthio-4-(5,6-dihydro-1,4,2!-dioxazin-3-yl)-pyrazole, 2-(5,6-dihydro-1,4,2!-dioxazin-3-yl)-3-benzylthio-thiophene.

The starting compounds of the formula (VII) are still not known from theliterature and, as novel compounds, are likewise a subject of thepresent invention.

A process for preparing the compounds of the formula (VII) is describedfurther below (cf. process (f)).

The following may be mentioned as examples of the chlorinating agentswhich are also to be used as starting compounds in process (d):

chlorine, sulphuryl chloride, alkali metal hypochlorite, chlorosulphonicacid.

The (het)arylsulphonamides to be used as starting compounds forpreparing compounds of the formula (II) in process (e) according to theinvention are defined generally by formula (VIII). In the formula(VIII), the group T has those preferred meanings which ensue from theabove definitions of the radicals E, R⁸, R¹⁰ and R¹³ contained therein.

The following may be mentioned as examples of the intermediates of theformula (VIII):

1-methyl-4-ethoxycarbonyl-pyrazole-5-sulphonamide,1-methyl-3-chloro-4-ethoxycarbonyl-pyrazole-5-sulphonamide,2-meth-oxycarbonylbenzenesulphonamide,(2-methoxycarbonylphenyl)methanesulphonamide,3-methoxycarbonylpyridine-2-sulphonamide and2-methoxycarbonylthiophene-3-sulphonamide.

The starting compounds of the formula (VIII) are known and/or can beprepared by processes which are known per se (cf., e.g., J. Heterocycl.Chem., 28(8), 1849-52, (1991); Pestic. Sci., 32(1), 91-104 (1991);Nippon Noyaku Gakkaishi, 15(4), 531-8 (1990); JP-63 051 394, JP-61 210003; Eur. J. Med Chem., 23(4), 329-34 (1988); ES-547 444, DE-2 706 859,DE-2 534 689).

The substituted alkanes which are additionally to be used as startingcompounds in process (e) are defined generally by the formula (IX). Informula (IX), the substituents R⁴, R⁵, R⁶ and R⁷ preferably or inparticular have those meanings which have already been indicated above,in connection with the description of the compounds of the formula (I),as being preferred or particularly preferred for R⁴ -R⁷ ; the reactive,vicinal leaving groups X and Y have the preferred meanings which havealready been indicated for formula (IX).

The following may be mentioned as examples of particularly suitablecompounds of the formula (IX):

1,2-dichloroethane, 1,2-dibromoethane, 1,2-diiodoethane,1,2-bis-(methanesulphonyloxy)ethane,1,2-bis-(trifluoromethanesulphonyloxy)ethane,1,2-bis-(trifluoroacetyloxy)ethane and1,2-bis-(4-toluenesulphonyloxy)ethane.

The starting compounds of the formula (IX) are known without exceptionand some of them are commercially available as chemicals for use insyntheses.

Finally, it has been found that the novel (het)arylthiobenzyl ethers ofthe above formula (VII), which are required for process (d), areobtained when

(f) (Het)arylthiobenzylcarboxylic esters of the formula (X) ##STR16## inwhich T has the meanings indicated above for process (e),

are reacted with hydroxylamine hydrochloride and a substituted alkane ofthe formula (IX), ##STR17## in which R⁴ -R⁷ have the above-indicatedmeanings, and

X and Y, independently of each other, represent halogen, or representalkylcarbonyloxy, arylcarbonyloxy, alkylsulphonyloxy orarylsulphonyloxy, which are optionally substituted (preferably representchlorine, bromine, iodine, C₁ -C₆ -alkylcarbonyloxy, C₆ -C₁₂-arylcarbonyloxy, C₁ -C₆ -alkylsulphonyloxy or C₆ -C₁₂-arylsulphonyloxy),

optionally in the presence of an organic diluent and optionally in thepresence of a reaction auxiliary.

If, for example, methyl 2-benzylmercaptobenzoate, hydroxylaminehydrochloride and 1,2-dibromoethane are used as starting compounds forprocess (f), the course of the reaction can then be outlined by thefollowing reaction scheme: ##STR18##

The (het)arylthiobenzylcarboxylic esters which are required as startingcompounds for preparing compounds of the formula (VII) in process (f)according to the invention are defined generally by formula (X); thatwhich has been said above in relation to process (e) applies for themeaning of the group T.

The following may be mentioned as examples of the intermediates of theformula (X):

methyl 2-benzylmercaptobenzoate, methyl2-benzylmercapto-6-methyl-benzoate, methyl(2-benzylmercaptophenyl)-acetate, methyl2-benzylmercaptopyridine-3-carboxylate, methyl1-methyl-5-benzylmercaptopyrazole-4-carboxylate, methyl1-methyl3-chloro-5-benzylmercaptopyrazole-4-carboxylate and methyl3-benzylmercaptothiophene-2-carboxylate.

The starting compounds of the formula (X) are known and/or can beprepared by processes which are known per se (cf, e.g., Chem. Pharm.Bull., 34(2), 540-9 (1986), J. Hetero-cycl. Chem. 15(3), 513-14 (1978)).

The substituted alkanes of the formula (IX) which are additionally to beused as starting compounds in process (f) have already been describedabove in more detail for process (e).

The processes (a), (b) and (c) according to the invention for preparingthe novel compounds (I), the processes (d) and (e) according to theinvention for preparing the novel intermediates of the formula (II), andthe process (f) according to the invention for preparing the novelintermediates of the formula (VII), are preferably carried out usingdiluents. In this context, practically all inert organic solvents aresuitable for use as diluents. These preferably include--except forprocess (d)--aliphatic and aromatic, optionally halogenatedhydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleumether, benzine, ligroin, benzene, toluene, xylene, methylene chloride,chlorobenzene and o-dichlorobenzene, ethers, such as diethyl ether anddibutyl ether, glycol dimethyl ether and diglycol dimethyl ether,tetrahydrofuran and dioxane, ketones, such as acetone, methyl ethylketone, methyl isopropyl ketone and methyl isobutyl ketone, esters, suchas methyl acetate and ethyl acetate, nitriles, such as, for example,acetonitrile and propionitrile, amides, such as, for example,dimethylformamide, dimethylacetamide and N-methylpyrrolidone, as well asdimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphorictriamide.

In the main, it is only the previously mentioned chlorinated solventswhich are suitable for use as diluents in the chlorination process (d).

The processes (a), (e) and (f) according to the invention are optionallycarried out in the presence of a reaction auxiliary. These preferablyinclude basic organic nitrogen compounds, such as, for example,trimethylamine, triethylamine, N,N-dimethylaniline,N,N-dimethylbenzylamine, pyridine, 4-dimethylaminopyridine,diazabicyclooctane (DABCO), diazabicyclononene (DBN) anddiazabicyclo-undecene (DBU), as well as inorganic bases, such as, forexample, sodium hydride, potassium hydride, sodium carbonate, potassiumcarbonate, calcium carbonate, potassium hydroxide, sodium hydroxide andcalcium hydroxide.

The processes (b) and (c) according to the invention are also optionallycarried out in the presence of a reaction auxiliary. Basic organicnitrogen compounds, such as, for example, trimethylamine, triethylamine,N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine,4-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene(DBN) and diazabicycloundecene (DBU), are suitable and preferred forthese processes.

The chlorinating process (d) can likewise be carried out in the presenceof a reaction auxiliary. Certain mineral and organic acids, such as, forexample, hydrochloric acid, dilute sulphuric acid, phosphoric acid,acetic acid or propionic acid, and, in addition, acidic salts, such as,for example, NaH₂ PO₄, are particularly suitable for this process.

In processes (a) to (f), the reaction temperatures may in each case bevaried over a relatively wide range. Thus

in process (a), temperatures of between 0° C. and 150° C., preferably ofbetween 10° C. and 80° C., are generally employed;

in process (b), temperatures of between 0° C. and 150° C., preferably ofbetween 20° C. and 100° C., are generally employed;

in process (c), temperatures of between 0° C. and 150° C., preferably ofbetween 20° C. and 100° C., are likewise generally employed;

in process (d), temperatures of between -20° C. and +40° C., preferablyof between -20° C. and +30° C., are generally employed;

in process (e), temperatures of between 0° C. and 150° C., preferably ofbetween 10° C. and 80° C., are generally employed, and

in process (f), temperatures of between 0° C. and 150° C., preferably ofbetween 10° C. and 80° C., are also generally employed.

The processes (a) to (f) are generally carried out under atmosphericpressure. However, it is in each case also possible to use elevated orreduced pressure.

In order to carry out processes (a) to (f) according to the invention,the starting compounds which are in each case required are employed inapproximately equimolar quantities. However, it is also possible to useone of the two components which are in each case employed in arelatively large excess. In general, the reactions are carried out in asuitable diluent and, where appropriate, with the addition of a reactionauxiliary, and the reaction mixture is stirred for several hours at thetemperature which is in each case required. In each of the processesaccording to the invention, working up is effected in accordance withcustomary methods.

Where appropriate, salts may be prepared from the compounds of thegeneral formula (I) according to the invention. Such salts are obtainedin a simple manner in accordance with customary salt-formation methods,for example by dissolving or dispersing a compound of the formula (I) ina suitable diluent, such as, for example, methylene chloride, acetone,tert-butyl methyl ether or toluene, and adding a suitable base. Thesalts may then be isolated--where appropriate after a relatively longperiod of stirring--by concentrating or by filtering off with suction(cf. the preparation examples).

The active compounds according to the invention can be used asdefoliants, desiccants, agents for destroying broad-leaved plants and,especially, as weed-killers. By weeds, in the broadest sense, there areto be understood all plants which grow in locations where they areundesired. Whether the substances according to the invention act astotal or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria,Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio,Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum,Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala,Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis,Papaver Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds are suitable, depending on the concentration, for thetotal combating of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for combating weeds in perennialcultures, for example afforestations, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, onornamental lawns and sports turf and on pasture land and for theselective combating of weeds in annual cultures.

The compounds of the formula (I) according to the invention can suitablybe used for selectively controlling monocotyledonous and dicotyledonousweeds in different cultures, in some cases, e.g. in wheat, both in thepreemergence process and in the postemergence process.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, suspensions, powders, foams, pastes,granules, aerosols, natural and synthetic materials impregnated withactive compound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquifiedgases under pressure, and/or solid carriers, optionally with use ofsurface-active agents, that is, emulsifying agents and/or dispersingagents, and/or foam-forming agents.

In the case of the use of water as an extender, organic solvents can,for example, also be used as auxiliary solvents. As liquid solvents,there are suitable in the main: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclo-hexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol as well as their ethers and esters, ketones, suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethyl-formamide ordimethyl sulphoxide, as well as water.

As solid carriers there are suitable: for example ammonium salts andground natural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silica, alumina and silicates; assolid carriers for granules there are suitable: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, as well as synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,maize cobs and tobacco stalks; as emulsifying and/or foamforming agentsthere are suitable: for example non-ionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as well as albumen hydrolysis products; asdispersing agents there are suitable: for example lignin-sulphite wasteliquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Further additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in their formulations, can also be used as mixtures withknown herbicides, finished formulations or tank mixes being possible.

Suitable herbicides for the mixtures are known herbicides, for exampleanilides such as, for example, diflufenican and propanil; arylcarboxylicacids such as, for example, dichloropicolinic acid, dicamba andpicloram; aryloxyalkanoic acids such as, for example, 2,4-D, 2,4-DB,2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoicesters such as, for example, diclofop-methyl, fenoxaprop-ethyl,fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones suchas, for example, chloridazon and norflurazon; carbamates such as, forexample, chloropropham, desmedipham, phenmedipham and prophamn;chloroacetanilides such as, for example, alachlor, acetochlor,butachlor, metazachlor, metolachlor, pretilachlor and propachlor,dinitroanilines such as, for example, oryzalin, pendimethalin andtrifluralin; diphenyl ethers such as, for example, acifluorfen, bifenox,fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureassuch as, for example, chlortoluron, diuron, fluometuron, isoproturon,linuron and methabenzthiazuron; hydroxylamines such as, for example,alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim;imidazolinones such as, for example, imazethapyr, imazamethabenz,imazapyr and imazaquin; nitriles such as, for example, bromoxynil,dichlobenil and ioxynil; oxyacetamides such as, for example, mefenacet;sulphonylureas such as, for example, amidosulfuron, bensulfuron-methyl,chlorimuron-ethyl, chlorsulfuron cinosulfuron, metsulfuron-methyl,nicosulfuron, primisulfuron, pyrazosulfuron-ethyl,thifensulfuron-methyl, triasulfuron and tribenuron-methyl,thiocarbamates such as, for example, butylate, cycloate, diallate, EPTC,esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazinessuch as, for example, atrazine, cyanazine, simazine, simetryn, terbutrynand terbutylazine; triazinones such as, for example, hexazinone,metamitron and metribuzin; others such as, for example, aminotriazole,benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat,dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate,isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repel-lents, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in customary manner, for example bywatering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a relatively largerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 10 g and 10 kg of active compoundper hectare of soil surface, preferably between 50 g and 5 kg perhectare.

The preparation and use of the active compounds according to theinvention can be seen from the following examples.

PREPARATION EXAMPLE Example I-1 ##STR19## (Process (a))

0.79 g (0.033 mol) of sodium hydride are added under argon to a mixtureof 4.0 g (0.017 mol) of 2-(5,6-dihydro-1,4,2!-dioxazin-3-yl)benzenesulphonamide and 4.6 g (0.017 mol) of2-phenoxycarbonylamino-4,6-dimethoxypyrimidine in 20 ml of absoluteacetonitrile, and the mixture is stirred at room temperature for 18hours. The precipitate is filtered off with suction and stirred up witha 20% solution of sodium dihydrogen phosphate. The precipitate isfiltered off with suction and dried under high vacuum. 3.9 g (56% oftheory) of N-(4,6-dimethoxypyrimidin-2-yl)-N'-(2-(5,6-dihydro-1,4,2!-dioxazin-3-yl)benzenesulphonyl)-urea are obtained with a meltingpoint of 189° C.

The additional compounds of the formula (I) listed in Tables 1, 2, 3 and4 below can also, for example, be prepared in analogy with Example I-1and in correspondence with the general description of the preparationprocesses according to the invention.

Abbreviations

m.p.:=melting point decomp. or d.=with decomposition.

.sup.(+) The melting point (m.p.) which is given relates in each case tothe corresponding sodium salt.

                  TABLE 1                                                         ______________________________________                                        Examples of compounds of the formula (I) having                               R.sup.4 = R.sup.5 = R.sup.6 = R.sup.7 = and R.sup.8 = CH.sub.3 : and          R.sup.10 = H:                                                                 Ex. No.                                                                             J     E       R.sup.1                                                                            A   R.sup.2                                                                              R.sup.3                                                                              m.p. (°C.)                  ______________________________________                                        I-1   J-1   --      H    CH  OCH.sub.3                                                                            OCH.sub.3                                                                            224                                                                           163.sup.(+)                        I-2   J-1   --      H    CH  OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                     176                                                                           70-71.sup.(+)                      I-3   J-1   --      H    CH  OCH.sub.3                                                                            CH.sub.3                                                                             145-146                                                                       157-163.sup.(+)                    I-4   J-1   --      H    CH  OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-5   J-1   --      H    CH  OCH.sub.3                                                                            CF.sub.3                                  I-6   J-1   --      H    CH  OCH.sub.3                                                                            OCF.sub.2 H                               I-7   J-1   --      H    CH  OCH.sub.3                                                                            NHCH.sub.3                                I-8   J-1   --      H    CH  OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                    192-193                            I-9   J-1   --      H    CH  OCH.sub.3                                                                            Cl     100-103                                                                       172-174.sup.(+)                    I-10  J-1   --      H    CH  OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          I-11  J-1   --      H    CH  OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-12  J-1   --      H    CH  OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-13  J-1   --      H    CH  OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-14  J-1   --      H    CH  OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-15  J-1   --      H    CH  OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-16  J-1   --      H    CH  OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-17  J-1   --      H    CH  OC.sub.2 H.sub.5                                                                     Cl     119-122                            I-18  J-1   --      H    CH  CH.sub.3                                                                             CH.sub.3                                                                             186-187                                                                       172-173.sup.(+)                    I-19  J-1   --      H    CH  CH.sub.3                                                                             C.sub.2 H.sub.5                           I-20  J-1   --      H    CH  CH.sub.3                                                                             CF.sub.3                                  I-21  J-1   --      H    CH  CH.sub.3                                                                             OCF.sub.2 H                               I-22  J-1   --      H    CH  CH.sub.3                                                                             NHCH.sub.3                                I-23  J-1   --      H    CH  CH.sub.3                                                                             N(CH.sub.3).sub.2                                                                    133                                                                           99.sup.(+)                         I-24  J-1   --      H    CH  CH.sub.3                                                                             Cl     146                                                                           110-111.sup.(+)                    I-25  J-1   --      H    CH  C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-26  J-1   --      H    CH  C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-27  J-1   --      H    CH  C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-28  J-1   --      H    CH  C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-29  J-1   --      H    CH  C.sub.2 H.sub.5                                                                      Cl                                        I-30  J-1   --      H    CH  CF.sub.3                                                                             CF.sub.3                                  I-31  J-1   --      H    CH  CF.sub.3                                                                             OCF.sub.2 H                               I-32  J-1   --      H    CH  CF.sub.3                                                                             NHCH.sub.3                                I-33  J-1   --      H    CH  CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-34  J-1   --      H    CH  CF.sub.3                                                                             Cl                                        I-35  J-1   --      H    CH  OCF.sub.2 H                                                                          OCF.sub.2 H                               I-36  J-1   --      H    CH  OCF.sub.2 H                                                                          NHCH.sub.3                                I-37  J-1   --      H    CH  OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-38  J-1   --      H    CH  OCF.sub.2 H                                                                          Cl                                        I-39  J-1   --      H    CH  NHCH.sub.3                                                                           NHCH.sub.3                                I-40  J-1   --      H    CH  NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-41  J-1   --      H    CH  NHCH.sub.3                                                                           Cl                                        I-42  J-1   --      H    CH  N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-43  J-1   --      H    CH  N(CH.sub.3).sub.2                                                                    Cl                                        I-44  J-1   --      H    CH  Cl     Cl                                        I-45  J-1   --      H    N   OCH.sub.3                                                                            OCH.sub.3                                                                            193                                I-46  J-1   --      H    N   OCH.sub.3                                                                            OC.sub.2 H.sub.5                          I-47  J-1   --      H    N   OCH.sub.3                                                                            CH.sub.3                                                                             190-192                                                                       178.sup.(+)                        I-48  J-1   --      H    N   OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-49  J-1   --      H    N   OCH.sub.3                                                                            CF.sub.3                                  I-50  J-1   --      H    N   OCH.sub.3                                                                            OCF.sub.2 H                               I-51  J-1   --      H    N   OCH.sub.3                                                                            NHCH.sub.3                                I-52  J-1   --      H    N   OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                    91-93                                                                         175.sup.(+)                        I-53  J-1   --      H    N   OCH.sub.3                                                                            Cl                                        I-54  J-1   --      H    N   OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          I-55  J-1   --      H    N   OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-56  J-1   --      H    N   OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-57  J-1   --      H    N   OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-58  J-1   --      H    N   OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-59  J-1   --      H    N   OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-60  J-1   --      H    N   OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-61  J-1   --      H    N   OC.sub.2 H.sub.5                                                                     Cl                                        I-62  J-1   --      H    N   CH.sub.3                                                                             CH.sub.3                                                                             179-181                                                                       168-172.sup.(+)                    I-63  J-1   --      H    N   CH.sub.3                                                                             C.sub.2 H.sub.5                           I-64  J-1   --      H    N   CH.sub.3                                                                             CF.sub.3                                  I-65  J-1   --      H    N   CH.sub.3                                                                             OCF.sub.2 H                               I-66  J-1   --      H    N   CH.sub.3                                                                             NHCH.sub.3                                I-67  J-1   --      H    N   CH.sub.3                                                                             N(CH.sub.3).sub.2                         I-68  J-1   --      H    N   CH.sub.3                                                                             Cl                                        I-69  J-1   --      H    N   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-70  J-1   --      H    N   C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-71  J-1   --      H    N   C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-72  J-1   --      H    N   C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-73  J-1   --      H    N   C.sub.2 H.sub.5                                                                      Cl                                        I-74  J-1   --      H    N   CF.sub.3                                                                             CF.sub.3                                  I-75  J-1   --      H    N   CF.sub.3                                                                             OCF.sub.2 H                               I-76  J-1   --      H    N   CF.sub.3                                                                             NHCH.sub.3                                I-77  J-1   --      H    N   CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-78  J-1   --      H    N   CF.sub.3                                                                             Cl                                        I-79  J-1   --      H    N   OCF.sub.2 H                                                                          OCF.sub.2 H                               I-80  J-1   --      H    N   OCF.sub.2 H                                                                          NHCH.sub.3                                I-81  J-1   --      H    N   OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-82  J-1   --      H    N   OCF.sub.2 H                                                                          Cl                                        I-83  J-1   --      H    N   NHCH.sub.3                                                                           NHCH.sub.3                                I-84  J-1   --      H    N   NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-85  J-1   --      H    N   NHCH.sub.3                                                                           Cl                                        I-86  J-1   --      H    N   N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-87  J-1   --      H    N   N(CH.sub.3).sub.2                                                                    Cl                                        I-88  J-1   --      H    N   Cl     Cl                                        I-89  J-1   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            OCH.sub.3                                                                            151-152.sup.(+)                    I-90  J-1   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            OC.sub.2 H.sub.5                          I-91  J-1   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            CH.sub.3                                  I-92  J-1   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-93  J-1   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            CF.sub.3                                  I-94  J-1   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            OCF.sub.2 H                               I-95  J-1   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            NHCH.sub.3                                I-96  J-1   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            N(CH.sub.3).sub.2                         I-97  J-1   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            Cl                                        I-98  J-1   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          I-99  J-1   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-100 J-1   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-101 J-1   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-102 J-1   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-103 J-1   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-104 J-1   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-105 J-1   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     Cl                                        I-106 J-1   --      CH.sub.3                                                                           N   CH.sub.3                                                                             CH.sub.3                                  I-107 J-1   --      CH.sub.3                                                                           N   CH.sub.3                                                                             C.sub.2 H.sub.5                           I-108 J-1   --      CH.sub.3                                                                           N   CH.sub.3                                                                             CF.sub.3                                  I-109 J-1   --      CH.sub.3                                                                           N   CH.sub.3                                                                             OCF.sub.2 H                               I-110 J-1   --      CH.sub.3                                                                           N   CH.sub.3                                                                             NHCH.sub.3                                I-111 J-1   --      CH.sub.3                                                                           N   CH.sub.3                                                                             N(CH.sub.3).sub.2                         I-112 J-1   --      CH.sub.3                                                                           N   CH.sub.3                                                                             Cl                                        I-113 J-1   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-114 J-1   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-115 J-1   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-116 J-1   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-117 J-1   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      Cl                                        I-118 J-1   --      CH.sub.3                                                                           N   CF.sub.3                                                                             CF.sub.3                                  I-119 J-1   --      CH.sub.3                                                                           N   CF.sub.3                                                                             OCF.sub.2 H                               I-120 J-1   --      CH.sub.3                                                                           N   CF.sub.3                                                                             NHCH.sub.3                                I-121 J-1   --      CH.sub.3                                                                           N   CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-122 J-1   --      CH.sub.3                                                                           N   CF.sub.3                                                                             Cl                                        I-123 J-1   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          OCF.sub.2 H                               I-124 J-1   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          NHCH.sub.3                                I-125 J-1   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-126 J-1   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          Cl                                        I-127 J-1   --      CH.sub.3                                                                           N   NHCH.sub.3                                                                           NHCH.sub.3                                I-128 J-1   --      CH.sub.3                                                                           N   NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-129 J-1   --      CH.sub.3                                                                           N   NHCH.sub.3                                                                           Cl                                        I-130 J-1   --      CH.sub.3                                                                           N   N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-131 J-1   --      CH.sub.3                                                                           N   N(CH.sub.3).sub.2                                                                    Cl                                        I-132 J-1   --      CH.sub.3                                                                           N   Cl     Cl                                        I-133 J-1   CH.sub.2 --                                                                           H    CH  OCH.sub.3                                                                            OCH.sub.3                                 I-134 J-1   CH.sub.2 --                                                                           H    CH  OCH.sub.3                                                                            OC.sub.2 H.sub.5                          I-135 J-1   CH.sub.2 --                                                                           H    CH  OCH.sub.3                                                                            CH.sub.3                                  I-136 J-1   CH.sub.2 --                                                                           H    CH  OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-137 J-1   CH.sub.2 --                                                                           H    CH  OCH.sub.3                                                                            CF.sub.3                                  I-138 J-1   CH.sub.2 --                                                                           H    CH  OCH.sub.3                                                                            OCF.sub.2 H                               I-139 J-1   CH.sub.2 --                                                                           H    CH  OCH.sub.3                                                                            NHCH.sub.3                                I-140 J-1   CH.sub.2 --                                                                           H    CH  OCH.sub.3                                                                            N(CH.sub.3).sub.2                         I-141 J-1   CH.sub.2 --                                                                           H    CH  OCH.sub.3                                                                            Cl                                        I-142 J-1   CH.sub.2 --                                                                           H    CH  OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          I-143 J-1   CH.sub.2 --                                                                           H    CH  OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-144 J-1   CH.sub.2 --                                                                           H    CH  OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-145 J-1   CH.sub.2 --                                                                           H    CH  OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-146 J-1   CH.sub.2 --                                                                           H    CH  OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-147 J-1   CH.sub.2 --                                                                           H    CH  OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-148 J-1   CH.sub.2 --                                                                           H    CH  OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-149 J-1   CH.sub.2 --                                                                           H    CH  OC.sub.2 H.sub.5                                                                     Cl                                        I-150 J-1   CH.sub.2 --                                                                           H    CH  CH.sub.3                                                                             CH.sub.3                                  I-151 J-1   CH.sub.2 --                                                                           H    CH  CH.sub.3                                                                             C.sub.2 H.sub.5                           I-152 J-1   CH.sub.2 --                                                                           H    CH  CH.sub.3                                                                             CF.sub.3                                  I-153 J-1   CH.sub.2 --                                                                           H    CH  CH.sub.3                                                                             OCF.sub.2 H                               I-154 J-1   CH.sub.2 --                                                                           H    CH  CH.sub.3                                                                             NHCH.sub.3                                I-155 J-1   CH.sub.2 --                                                                           H    CH  CH.sub.3                                                                             N(CH.sub.3).sub.2                         I-156 J-1   CH.sub.2 --                                                                           H    CH  CH.sub.3                                                                             Cl                                        I-157 J-1   CH.sub.2 --                                                                           H    CH  C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-158 J-1   CH.sub.2 --                                                                           H    CH  C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-159 J-1   CH.sub.2 --                                                                           H    CH  C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-160 J-1   CH.sub.2 --                                                                           H    CH  C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-161 J-1   CH.sub.2 --                                                                           H    CH  C.sub.2 H.sub.5                                                                      Cl                                        I-162 J-1   CH.sub.2 --                                                                           H    CH  CF.sub.3                                                                             CF.sub.3                                  I-163 J-1   CH.sub.2 --                                                                           H    CH  CF.sub.3                                                                             OCF.sub.2 H                               I-164 J-1   CH.sub.2 --                                                                           H    CH  CF.sub.3                                                                             NHCH.sub.3                                I-165 J-1   CH.sub.2 --                                                                           H    CH  CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-166 J-1   CH.sub.2 --                                                                           H    CH  CF.sub.3                                                                             Cl                                        I-167 J-1   CH.sub.2 --                                                                           H    CH  OCF.sub.2 H                                                                          OCF.sub.2 H                               I-168 J-1   CH.sub.2 --                                                                           H    CH  OCF.sub.2 H                                                                          NHCH.sub.3                                I-169 J-1   CH.sub.2 --                                                                           H    CH  OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-170 J-1   CH.sub.2 --                                                                           H    CH  OCF.sub.2 H                                                                          Cl                                        I-171 J-1   CH.sub.2 --                                                                           H    CH  NHCH.sub.3                                                                           NHCH.sub.3                                I-172 J-1   CH.sub.2 --                                                                           H    CH  NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-173 J-1   CH.sub.2 --                                                                           H    CH  NHCH.sub.3                                                                           Cl                                        I-174 J-1   CH.sub.2 --                                                                           H    CH  N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-175 J-1   CH.sub.2 --                                                                           H    CH  N(CH.sub.3).sub.2                                                                    Cl                                        I-176 J-1   CH.sub.2 --                                                                           H    CH  Cl     Cl                                        I-177 J-1   CH.sub.2 --                                                                           H    N   OCH.sub.3                                                                            OCH.sub.3                                 I-178 J-1   CH.sub.2 --                                                                           H    N   OCH.sub.3                                                                            OC.sub.2 H.sub.5                          I-179 J-1   CH.sub.2 --                                                                           H    N   OCH.sub.3                                                                            CH.sub.3                                  I-180 J-1   CH.sub.2 --                                                                           H    N   OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-181 J-1   CH.sub.2 --                                                                           H    N   OCH.sub.3                                                                            CF.sub.3                                  I-182 J-1   CH.sub.2 --                                                                           H    N   OCH.sub.3                                                                            OCF.sub.2 H                               I-183 J-1   CH.sub.2 --                                                                           H    N   OCH.sub.3                                                                            NHCH.sub.3                                I-184 J-1   CH.sub.2 --                                                                           H    N   OCH.sub.3                                                                            N(CH.sub.3).sub.2                         I-185 J-1   CH.sub.2 --                                                                           H    N   OCH.sub.3                                                                            Cl                                        I-186 J-1   CH.sub.2 --                                                                           H    N   OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          I-187 J-1   CH.sub.2 --                                                                           H    N   OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-188 J-1   CH.sub.2 --                                                                           H    N   OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-189 J-1   CH.sub.2 --                                                                           H    N   OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-190 J-1   CH.sub.2 --                                                                           H    N   OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-191 J-1   CH.sub.2 --                                                                           H    N   OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-192 J-1   CH.sub.2 --                                                                           H    N   OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-193 J-1   CH.sub.2 --                                                                           H    N   OC.sub.2 H.sub.5                                                                     Cl                                        I-194 J-1   CH.sub.2 --                                                                           H    N   CH.sub.3                                                                             CH.sub.3                                  I-195 J-1   CH.sub.2 --                                                                           H    N   CH.sub.3                                                                             C.sub.2 H.sub.5                           I-196 J-1   CH.sub.2 --                                                                           H    N   CH.sub.3                                                                             CF.sub.3                                  I-197 J-1   CH.sub.2 --                                                                           H    N   CH.sub.3                                                                             OCF.sub.2 H                               I-198 J-1   CH.sub.2 --                                                                           H    N   CH.sub.3                                                                             NHCH.sub.3                                I-199 J-1   CH.sub.2 --                                                                           H    N   CH.sub.3                                                                             N(CH.sub.3).sub.2                         I-200 J-1   CH.sub.2 --                                                                           H    N   CH.sub.3                                                                             Cl                                        I-201 J-1   CH.sub.2 --                                                                           H    N   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-202 J-1   CH.sub.2 --                                                                           H    N   C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-203 J-1   CH.sub.2 --                                                                           H    N   C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-204 J-1   CH.sub.2 --                                                                           H    N   C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-205 J-1   CH.sub.2 --                                                                           H    N   C.sub.2 H.sub.5                                                                      Cl                                        I-206 J-1   CH.sub.2 --                                                                           H    N   CF.sub.3                                                                             CF.sub.3                                  I-207 J-1   CH.sub.2 --                                                                           H    N   CF.sub.3                                                                             OCF.sub.2 H                               I-208 J-1   CH.sub.2 --                                                                           H    N   CF.sub.3                                                                             NHCH.sub.3                                I-209 J-1   CH.sub.2 --                                                                           H    N   CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-210 J-1   CH.sub.2 --                                                                           H    N   CF.sub.3                                                                             Cl                                        I-211 J-1   CH.sub.2 --                                                                           H    N   OCF.sub.2 H                                                                          OCF.sub.2 H                               I-212 J-1   CH.sub.2 --                                                                           H    N   OCF.sub.2 H                                                                          NHCH.sub.3                                I-213 J-1   CH.sub.2 --                                                                           H    N   OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-214 J-1   CH.sub.2 --                                                                           H    N   OCF.sub.2 H                                                                          Cl                                        I-215 J-1   CH.sub.2 --                                                                           H    N   NHCH.sub.3                                                                           NHCH.sub.3                                I-216 J-1   CH.sub.2 --                                                                           H    N   NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-217 J-1   CH.sub.2 --                                                                           H    N   NHCH.sub.3                                                                           Cl                                        I-218 J-1   CH.sub.2 --                                                                           H    N   N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-219 J-1   CH.sub.2 --                                                                           H    N   N(CH.sub.3).sub.2                                                                    Cl                                        I-220 J-1   CH.sub.2 --                                                                           H    N   Cl     Cl                                        I-221 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OCH.sub.3                                                                            OCH.sub.3                                 I-222 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OCH.sub.3                                                                            OC.sub.2 H.sub.5                          I-223 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OCH.sub.3                                                                            CH.sub.3                                  I-224 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-225 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OCH.sub.3                                                                            CF.sub.3                                  I-226 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OCH.sub.3                                                                            OCF.sub.2 H                               I-227 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OCH.sub.3                                                                            NHCH.sub.3                                I-228 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OCH.sub.3                                                                            N(CH.sub.3).sub.2                         I-229 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OCH.sub.3                                                                            Cl                                        I-230 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          I-231 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-232 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-233 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-234 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-235 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-236 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-237 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     Cl                                        I-238 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   CH.sub.3                                                                             CH.sub.3                                  I-239 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   CH.sub.3                                                                             C.sub.2 H.sub.5                           I-240 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   CH.sub.3                                                                             CF.sub.3                                  I-241 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   CH.sub.3                                                                             OCF.sub.2 H                               I-242 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   CH.sub.3                                                                             NHCH.sub.3                                I-243 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   CH.sub.3                                                                             N(CH.sub.3).sub.2                         I-244 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   CH.sub.3                                                                             Cl                                        I-245 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-246 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-247 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-248 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-249 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      Cl                                        I-250 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   CF.sub.3                                                                             CF.sub.3                                  I-251 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   CF.sub.3                                                                             OCF.sub.2 H                               I-252 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   CF.sub.3                                                                             NHCH.sub.3                                I-253 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-254 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   CF.sub.3                                                                             Cl                                        I-255 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OCF.sub.2 H                                                                          OCF.sub.2 H                               I-256 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OCF.sub.2 H                                                                          NHCH.sub.3                                I-257 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-258 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   OCF.sub.2 H                                                                          Cl                                        I-259 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   NHCH.sub.3                                                                           NHCH.sub.3                                I-260 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-261 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   NHCH.sub.3                                                                           Cl                                        I-262 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-263 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   N(CH.sub.3).sub.2                                                                    Cl                                        I-264 J-1   CH.sub.2 --                                                                           CH.sub.3                                                                           N   Cl     Cl                                        I-265 J-2   --      H    CH  OCH.sub.3                                                                            OCH.sub.3                                                                            167-168                                                                       171-172.sup.(+)                    I-266 J-2   --      H    CH  OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                     154                                I-267 J-2   --      H    CH  OCH.sub.3                                                                            CH.sub.3                                                                             180-181.sup.(+)                    I-268 J-2   --      H    CH  OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-269 J-2   --      H    CH  OCH.sub.3                                                                            CF.sub.3                                  I-270 J-2   --      H    CH  OCH.sub.3                                                                            OCF.sub.2 H                               I-271 J-2   --      H    CH  OCH.sub.3                                                                            NHCH.sub.3                                I-272 J-2   --      H    CH  OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                    199, 5                             I-273 J-2   --      H    CH  OCH.sub.3                                                                            Cl     110-111                                                                       175-178.sup.(+)                    I-274 J-2   --      H    CH  OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                     152-154.sup.(+)                    I-275 J-2   --      H    CH  OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-276 J-2   --      H    CH  OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-277 J-2   --      H    CH  OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-278 J-2   --      H    CH  OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-279 J-2   --      H    CH  OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-280 J-2   --      H    CH  OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-281 J-2   --      H    CH  OC.sub.2 H.sub.5                                                                     Cl     158-159                                                                       213.sup.(+)                        I-282 J-2   --      H    CH  CH.sub.3                                                                             CH.sub.3                                                                             153                                I-283 J-2   --      H    CH  CH.sub.3                                                                             C.sub.2 H.sub.5                           I-284 J-2   --      H    CH  CH.sub.3                                                                             CF.sub.3                                  I-285 J-2   --      H    CH  CH.sub.3                                                                             OCF.sub.2 H                               I-286 J-2   --      H    CH  CH.sub.3                                                                             NHCH.sub.3                                I-287 J-2   --      H    CH  CH.sub.3                                                                             N(CH.sub.3).sub.2                         I-288 J-2   --      H    CH  CH.sub.3                                                                             Cl     108-109                                                                       >300.sup.(+)                       I-289 J-2   --      H    CH  C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-290 J-2   --      H    CH  C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-291 J-2   --      H    CH  C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-292 J-2   --      H    CH  C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-293 J-2   --      H    CH  C.sub.2 H.sub.5                                                                      Cl                                        I-294 J-2   --      H    CH  CF.sub.3                                                                             CF.sub.3                                  I-295 J-2   --      H    CH  CF.sub.3                                                                             OCF.sub.2 H                               I-296 J-2   --      H    CH  CF.sub.3                                                                             NHCH.sub.3                                I-297 J-2   --      H    CH  CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-298 J-2   --      H    CH  CF.sub.3                                                                             Cl                                        I-299 J-2   --      H    CH  OCF.sub.2 H                                                                          OCF.sub.2 H                               I-300 J-2   --      H    CH  OCF.sub.2 H                                                                          NHCH.sub.3                                I-301 J-2   --      H    CH  OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-302 J-2   --      H    CH  OCF.sub.2 H                                                                          Cl                                        I-303 J-2   --      H    CH  NHCH.sub.3                                                                           NHCH.sub.3                                I-304 J-2   --      H    CH  NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-305 J-2   --      H    CH  NHCH.sub.3                                                                           Cl                                        I-306 J-2   --      H    CH  N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-307 J-2   --      H    CH  N(CH.sub.3).sub.2                                                                    Cl                                        I-308 J-2   --      H    CH  Cl     Cl                                        I-309 J-2   --      H    N   OCH.sub.3                                                                            OCH.sub.3                                                                            255                                                                           159-162.sup.(+)                    I-310 J-2   --      H    N   OCH.sub.3                                                                            OC.sub.2 H.sub.5                          I-311 J-2   --      H    N   OCH.sub.3                                                                            CH.sub.3                                  I-312 J-2   --      H    N   OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-313 J-2   --      H    N   OCH.sub.3                                                                            CF.sub.3                                  I-314 J-2   --      H    N   OCH.sub.3                                                                            OCF.sub.2 H                               I-315 J-2   --      H    N   OCH.sub.3                                                                            NHCH.sub.3                                I-316 J-2   --      H    N   OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                    156.sup.(+)                        I-317 J-2   --      H    N   OCH.sub.3                                                                            Cl                                        I-318 J-2   --      H    N   OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          I-319 J-2   --      H    N   OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-320 J-2   --      H    N   OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-321 J-2   --      H    N   OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-322 J-2   --      H    N   OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-323 J-2   --      H    N   OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-324 J-2   --      H    N   OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-325 J-2   --      H    N   OC.sub.2 H.sub.5                                                                     Cl     213.sup.(+)                        I-326 J-2   --      H    N   CH.sub.3                                                                             CH.sub.3                                  I-327 J-2   --      H    N   CH.sub.3                                                                             C.sub.2 H.sub.5                           I-328 J-2   --      H    N   CH.sub.3                                                                             CF.sub.3                                  I-329 J-2   --      H    N   CH.sub.3                                                                             OCF.sub.2 H                               I-330 J-2   --      H    N   CH.sub.3                                                                             NHCH.sub.3                                I-331 J-2   --      H    N   CH.sub.3                                                                             N(CH.sub.3).sub.2                         I-332 J-2   --      H    N   CH.sub.3                                                                             Cl                                        I-333 J-2   --      H    N   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-334 J-2   --      H    N   C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-335 J-2   --      H    N   C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-336 J-2   --      H    N   C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-337 J-2   --      H    N   C.sub.2 H.sub.5                                                                      Cl                                        I-338 J-2   --      H    N   CF.sub.3                                                                             CF.sub.3                                  I-339 J-2   --      H    N   CF.sub.3                                                                             OCF.sub.2 H                               I-340 J-2   --      H    N   CF.sub.3                                                                             NHCH.sub.3                                I-341 J-2   --      H    N   CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-342 J-2   --      H    N   CF.sub.3                                                                             Cl                                        I-343 J-2   --      H    N   OCF.sub.2 H                                                                          OCF.sub.2 H                               I-344 J-2   --      H    N   OCF.sub.2 H                                                                          NHCH.sub.3                                I-345 J-2   --      H    N   OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-346 J-2   --      H    N   OCF.sub.2 H                                                                          Cl                                        I-347 J-2   --      H    N   NHCH.sub.3                                                                           NHCH.sub.3                                I-348 J-2   --      H    N   NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-349 J-2   --      H    N   NHCH.sub.3                                                                           Cl                                        I-350 J-2   --      H    N   N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-351 J-2   --      H    N   N(CH.sub.3).sub.2                                                                    Cl                                        I-352 J-2   --      H    N   Cl     Cl                                        I-353 J-2   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            OCH.sub.3                                 I-354 J-2   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            OC.sub.2 H.sub.5                          I-355 J-2   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            CH.sub.3                                  I-356 J-2   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-357 J-2   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            CF.sub.3                                  I-358 J-2   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            OCF.sub.2 H                               I-359 J-2   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            NHCH.sub.3                                I-360 J-2   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            N(CH.sub.3).sub.2                         I-361 J-2   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            Cl                                        I-362 J-2   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          I-363 J-2   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-364 J-2   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-365 J-2   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-366 J-2   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-367 J-2   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-368 J-2   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-369 J-2   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     Cl                                        I-370 J-2   --      CH.sub.3                                                                           N   CH.sub.3                                                                             CH.sub.3                                  I-371 J-2   --      CH.sub.3                                                                           N   CH.sub.3                                                                             C.sub.2 H.sub.5                           I-372 J-2   --      CH.sub.3                                                                           N   CH.sub.3                                                                             CF.sub.3                                  I-373 J-2   --      CH.sub.3                                                                           N   CH.sub.3                                                                             OCF.sub.2 H                               I-374 J-2   --      CH.sub.3                                                                           N   CH.sub.3                                                                             NHCH.sub.3                                I-375 J-2   --      CH.sub.3                                                                           N   CH.sub.3                                                                             N(CH.sub.3).sub.2                         I-376 J-2   --      CH.sub.3                                                                           N   CH.sub.3                                                                             Cl                                        I-377 J-2   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-378 J-2   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-379 J-2   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-380 J-2   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-381 J-2   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      Cl                                        I-382 J-2   --      CH.sub.3                                                                           N   CF.sub.3                                                                             CF.sub.3                                  I-383 J-2   --      CH.sub.3                                                                           N   CF.sub.3                                                                             OCF.sub.2 H                               I-384 J-2   --      CH.sub.3                                                                           N   CF.sub.3                                                                             NHCH.sub.3                                I-385 J-2   --      CH.sub.3                                                                           N   CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-386 J-2   --      CH.sub.3                                                                           N   CF.sub.3                                                                             Cl                                        I-387 J-2   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          OCF.sub.2 H                               I-388 J-2   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          NHCH.sub.3                                I-389 J-2   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-390 J-2   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          Cl                                        I-391 J-2   --      CH.sub.3                                                                           N   NHCH.sub.3                                                                           NHCH.sub.3                                I-392 J-2   --      CH.sub.3                                                                           N   NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-393 J-2   --      CH.sub.3                                                                           N   NHCH.sub.3                                                                           Cl                                        I-394 J-2   --      CH.sub.3                                                                           N   N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-395 J-2   --      CH.sub.3                                                                           N   N(CH.sub.3).sub.2                                                                    Cl                                        I-396 J-2   --      CH.sub.3                                                                           N   Cl     Cl                                        I-397 J-3   --      H    CH  OCH.sub.3                                                                            OCH.sub.3                                                                            250                                                                           (d.).sup.(+)                       I-398 J-3   --      H    CH  OCH.sub.3                                                                            OC.sub.2 H.sub.5                          I-399 J-3   --      H    CH  OCH.sub.3                                                                            CH.sub.3                                  I-400 J-3   --      H    CH  OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-401 J-3   --      H    CH  OCH.sub.3                                                                            CF.sub.3                                  I-402 J-3   --      H    CH  OCH.sub.3                                                                            OCF.sub.2 H                               I-403 J-3   --      H    CH  OCH.sub.3                                                                            NHCH.sub.3                                I-404 J-3   --      H    CH  OCH.sub.3                                                                            N(CH.sub.3).sub.2                         I-405 J-3   --      H    CH  OCH.sub.3                                                                            Cl                                        I-406 J-3   --      H    CH  OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          I-407 J-3   --      H    CH  OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-408 J-3   --      H    CH  OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-409 J-3   --      H    CH  OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-410 J-3   --      H    CH  OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-411 J-3   --      H    CH  OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-412 J-3   --      H    CH  OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-413 J-3   --      H    CH  OC.sub.2 H.sub.5                                                                     Cl                                        I-414 J-3   --      H    CH  CH.sub.3                                                                             CH.sub.3                                                                             180-2                              I-415 J-3   --      H    CH  CH.sub.3                                                                             C.sub.2 H.sub.5                           I-416 J-3   --      H    CH  CH.sub.3                                                                             CF.sub.3                                  I-417 J-3   --      H    CH  CH.sub.3                                                                             OCF.sub.2 H                               I-418 J-3   --      H    CH  CH.sub.3                                                                             NHCH.sub.3                                I-419 J-3   --      H    CH  CH.sub.3                                                                             N(CH.sub.3).sub.2                         I-420 J-3   --      H    CH  CH.sub.3                                                                             Cl                                        I-421 J-3   --      H    CH  C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-422 J-3   --      H    CH  C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-423 J-3   --      H    CH  C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-424 J-3   --      H    CH  C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-425 J-3   --      H    CH  C.sub.2 H.sub.5                                                                      Cl                                        I-426 J-3   --      H    CH  CF.sub.3                                                                             CF.sub.3                                  I-427 J-3   --      H    CH  CF.sub.3                                                                             OCF.sub.2 H                               I-428 J-3   --      H    CH  CF.sub.3                                                                             NHCH.sub.3                                I-429 J-3   --      H    CH  CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-430 J-3   --      H    CH  CF.sub.3                                                                             Cl                                        I-431 J-3   --      H    CH  OCF.sub.2 H                                                                          OCF.sub.2 H                               I-432 J-3   --      H    CH  OCF.sub.2 H                                                                          NHCH.sub.3                                I-433 J-3   --      H    CH  OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-434 J-3   --      H    CH  OCF.sub.2 H                                                                          Cl                                        I-435 J-3   --      H    CH  NHCH.sub.3                                                                           NHCH.sub.3                                I-436 J-3   --      H    CH  NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-437 J-3   --      H    CH  NHCH.sub.3                                                                           Cl                                        I-438 J-3   --      H    CH  N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-439 J-3   --      H    CH  N(CH.sub.3).sub.2                                                                    Cl                                        I-440 J-3   --      H    CH  Cl     Cl                                        I-441 J-3   --      H    N   OCH.sub.3                                                                            OCH.sub.3                                                                            169-72                                                                        (d.)                               I-442 J-3   --      H    N   OCH.sub.3                                                                            OC.sub.2 H.sub.5                          I-443 J-3   --      H    N   OCH.sub.3                                                                            CH.sub.3                                                                             190-2.sup.(+)                      I-444 J-3   --      H    N   OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-445 J-3   --      H    N   OCH.sub.3                                                                            CF.sub.3                                  I-446 J-3   --      H    N   OCH.sub.3                                                                            OCF.sub.2 H                               I-447 J-3   --      H    N   OCH.sub.3                                                                            NHCH.sub.3                                I-448 J-3   --      H    N   OCH.sub.3                                                                            N(CH.sub.3).sub.2                         I-449 J-3   --      H    N   OCH.sub.3                                                                            Cl                                        I-450 J-3   --      H    N   OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          I-451 J-3   --      H    N   OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-452 J-3   --      H    N   OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-453 J-3   --      H    N   OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-454 J-3   --      H    N   OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-455 J-3   --      H    N   OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-456 J-3   --      H    N   OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-457 J-3   --      H    N   OC.sub.2 H.sub.5                                                                     Cl                                        I-458 J-3   --      H    N   CH.sub.3                                                                             CH.sub.3                                  I-459 J-3   --      H    N   CH.sub.3                                                                             C.sub.2 H.sub.5                           I-460 J-3   --      H    N   CH.sub.3                                                                             CF.sub.3                                  I-461 J-3   --      H    N   CH.sub.3                                                                             OCF.sub.2 H                               I-462 J-3   --      H    N   CH.sub.3                                                                             NHCH.sub.3                                I-463 J-3   --      H    N   CH.sub.3                                                                             N(CH.sub.3).sub.2                         I-464 J-3   --      H    N   CH.sub.3                                                                             Cl                                        I-465 J-3   --      H    N   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-466 J-3   --      H    N   C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-467 J-3   --      H    N   C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-468 J-3   --      H    N   C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-469 J-3   --      H    N   C.sub.2 H.sub.5                                                                      Cl                                        I-470 J-3   --      H    N   CF.sub.3                                                                             CF.sub.3                                  I-471 J-3   --      H    N   CF.sub.3                                                                             OCF.sub.2 H                               I-472 J-3   --      H    N   CF.sub.3                                                                             NHCH.sub.3                                I-473 J-3   --      H    N   CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-474 J-3   --      H    N   CF.sub.3                                                                             Cl                                        I-475 J-3   --      H    N   OCF.sub.2 H                                                                          OCF.sub.2 H                               I-476 J-3   --      H    N   OCF.sub.2 H                                                                          NHCH.sub.3                                I-477 J-3   --      H    N   OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-478 J-3   --      H    N   OCF.sub.2 H                                                                          Cl                                        I-479 J-3   --      H    N   NHCH.sub.3                                                                           NHCH.sub.3                                I-480 J-3   --      H    N   NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-481 J-3   --      H    N   NHCH.sub.3                                                                           Cl                                        I-482 J-3   --      H    N   N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-483 J-3   --      H    N   N(CH.sub.3).sub.2                                                                    Cl                                        I-484 J-3   --      H    N   Cl     Cl                                        I-485 J-3   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            OCH.sub.3                                                                            204                                                                           (de-comp.)                         I-486 J-3   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            OC.sub.2 H.sub.5                          I-487 J-3   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            CH.sub.3                                  I-488 J-3   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-489 J-3   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            CF.sub.3                                  I-490 J-3   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            OCF.sub.2 H                               I-491 J-3   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            NHCH.sub.3                                I-492 J-3   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            N(CH.sub.3).sub.2                         I-493 J-3   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            Cl                                        I-494 J-3   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          I-495 J-3   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-496 J-3   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-497 J-3   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-498 J-3   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-499 J-3   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-500 J-3   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-501 J-3   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     Cl                                        I-502 J-3   --      CH.sub.3                                                                           N   CH.sub.3                                                                             CH.sub.3                                  I-503 J-3   --      CH.sub.3                                                                           N   CH.sub.3                                                                             C.sub.2 H.sub.5                           I-504 J-3   --      CH.sub.3                                                                           N   CH.sub.3                                                                             CF.sub.3                                  I-505 J-3   --      CH.sub.3                                                                           N   CH.sub.3                                                                             OCF.sub.2 H                               I-506 J-3   --      CH.sub.3                                                                           N   CH.sub.3                                                                             NHCH.sub.3                                I-507 J-3   --      CH.sub.3                                                                           N   CH.sub.3                                                                             N(CH.sub.3).sub.2                         I-508 J-3   --      CH.sub.3                                                                           N   CH.sub.3                                                                             Cl                                        I-509 J-3   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-510 J-3   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-511 J-3   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-512 J-3   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-513 J-3   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      Cl                                        I-514 J-3   --      CH.sub.3                                                                           N   CF.sub.3                                                                             CF.sub.3                                  I-515 J-3   --      CH.sub.3                                                                           N   CF.sub.3                                                                             OCF.sub.2 H                               I-516 J-3   --      CH.sub.3                                                                           N   CF.sub.3                                                                             NHCH.sub.3                                I-517 J-3   --      CH.sub.3                                                                           N   CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-518 J-3   --      CH.sub.3                                                                           N   CF.sub.3                                                                             Cl                                        I-519 J-3   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          OCF.sub.2 H                               I-520 J-3   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          NHCH.sub.3                                I-521 J-3   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-522 J-3   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          Cl                                        I-523 J-3   --      CH.sub.3                                                                           N   NHCH.sub.3                                                                           NHCH.sub.3                                I-524 J-3   --      CH.sub.3                                                                           N   NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-525 J-3   --      CH.sub.3                                                                           N   NHCH.sub.3                                                                           Cl                                        I-526 J-3   --      CH.sub.3                                                                           N   N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-527 J-3   --      CH.sub.3                                                                           N   N(CH.sub.3).sub.2                                                                    Cl                                        I-528 J-3   --      CH.sub.3                                                                           N   Cl     Cl                                        I-529 J-4   --      H    CH  OCH.sub.3                                                                            OCH.sub.3                                                                            185-186                                                                       151-152.sup.(+)                    I-530 J-4   --      H    CH  OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                     174-175                                                                       85.sup.(+)                         I-531 J-4   --      H    CH  OCH.sub.3                                                                            CH.sub.3                                                                             178                                                                           165-167.sup.(+)                    I-532 J-4   --      H    CH  OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-533 J-4   --      H    CH  OCH.sub.3                                                                            CF.sub.3                                  I-534 J-4   --      H    CH  OCH.sub.3                                                                            OCF.sub.2 H                               I-535 J-4   --      H    CH  OCH.sub.3                                                                            NHCH.sub.3                                I-536 J-4   --      H    CH  OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                    92-95                                                                         258-262.sup.(+)                    I-537 J-4   --      H    CH  OCH.sub.3                                                                            Cl     112                                                                           185-186.sup.(+)                    I-538 J-4   --      H    CH  OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                     134-137                            I-539 J-4   --      H    CH  OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-540 J-4   --      H    CH  OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-541 J-4   --      H    CH  OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-542 J-4   --      H    CH  OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-543 J-4   --      H    CH  OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-544 J-4   --      H    CH  OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-545 J-4   --      H    CH  OC.sub.2 H.sub.5                                                                     Cl     181-183                                                                       171.sup.(+)                        I-546 J-4   --      H    CH  CH.sub.3                                                                             CH.sub.3                                                                             195                                                                           230-232.sup.(+)                    I-547 J-4   --      H    CH  CH.sub.3                                                                             C.sub.2 H.sub.5                           I-548 J-4   --      H    CH  CH.sub.3                                                                             CF.sub.3                                  I-549 J-4   --      H    CH  CH.sub.3                                                                             OCF.sub.2 H                               I-550 J-4   --      H    CH  CH.sub.3                                                                             NHCH.sub.3                                I-551 J-4   --      H    CH  CH.sub.3                                                                             N(CH.sub.3).sub.2                         I-552 J-4   --      H    CH  CH.sub.3                                                                             Cl     175                                                                           138-140.sup.(+)                    I-553 J-4   --      H    CH  C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-554 J-4   --      H    CH  C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-555 J-4   --      H    CH  C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-556 J-4   --      H    CH  C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-557 J-4   --      H    CH  C.sub.2 H.sub.5                                                                      Cl                                        I-558 J-4   --      H    CH  CF.sub.3                                                                             CF.sub.3                                  I-559 J-4   --      H    CH  CF.sub.3                                                                             OCF.sub.2 H                               I-560 J-4   --      H    CH  CF.sub.3                                                                             NHCH.sub.3                                I-561 J-4   --      H    CH  CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-562 J-4   --      H    CH  CF.sub.3                                                                             Cl                                        I-563 J-4   --      H    CH  OCF.sub.2 H                                                                          OCF.sub.2 H                               I-564 J-4   --      H    CH  OCF.sub.2 H                                                                          NHCH.sub.3                                I-565 J-4   --      H    CH  OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-566 J-4   --      H    CH  OCF.sub.2 H                                                                          Cl                                        I-567 J-4   --      H    CH  NHCH.sub.3                                                                           NHCH.sub.3                                I-568 J-4   --      H    CH  NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-569 J-4   --      H    CH  NHCH.sub.3                                                                           Cl                                        I-570 J-4   --      H    CH  N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-571 J-4   --      H    CH  N(CH.sub.3).sub.2                                                                    Cl                                        I-572 J-4   --      H    CH  Cl     Cl                                        I-573 J-4   --      H    N   OCH.sub.3                                                                            OCH.sub.3                                                                            179                                I-574 J-4   --      H    N   OCH.sub.3                                                                            OC.sub.2 H.sub.5                          I-575 J-4   --      H    N   OCH.sub.3                                                                            CH.sub.3                                                                             238.sup.(+)                        I-576 J-4   --      H    N   OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-577 J-4   --      H    N   OCH.sub.3                                                                            CF.sub.3                                  I-578 J-4   --      H    N   OCH.sub.3                                                                            OCF.sub.2 H                               I-579 J-4   --      H    N   OCH.sub.3                                                                            NHCH.sub.3                                I-580 J-4   --      H    N   OCH.sub.3                                                                            N(CH.sub.3).sub.2                         I-581 J-4   --      H    N   OCH.sub.3                                                                            Cl                                        I-582 J-4   --      H    N   OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          I-583 J-4   --      H    N   OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-584 J-4   --      H    N   OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-585 J-4   --      H    N   OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-586 J-4   --      H    N   OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-587 J-4   --      H    N   OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-588 J-4   --      H    N   OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-589 J-4   --      H    N   OC.sub.2 H.sub.5                                                                     Cl                                        I-590 J-4   --      H    N   CH.sub.3                                                                             CH.sub.3                                                                             200                                                                           177-178.sup.(+)                    I-591 J-4   --      H    N   CH.sub.3                                                                             C.sub.2 H.sub.5                           I-592 J-4   --      H    N   CH.sub.3                                                                             CF.sub.3                                  I-593 J-4   --      H    N   CH.sub.3                                                                             OCF.sub.2 H                               I-594 J-4   --      H    N   CH.sub.3                                                                             NHCH.sub.3                                I-595 J-4   --      H    N   CH.sub.3                                                                             N(CH.sub.3).sub.2                         I-596 J-4   --      H    N   CH.sub.3                                                                             Cl                                        I-597 J-4   --      H    N   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-598 J-4   --      H    N   C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-599 J-4   --      H    N   C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-600 J-4   --      H    N   C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-601 J-4   --      H    N   C.sub.2 H.sub.5                                                                      Cl                                        I-602 J-4   --      H    N   CF.sub.3                                                                             CF.sub.3                                  I-603 J-4   --      H    N   CF.sub.3                                                                             OCF.sub.2 H                               I-604 J-4   --      H    N   CF.sub.3                                                                             NHCH.sub.3                                I-605 J-4   --      H    N   CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-606 J-4   --      H    N   CF.sub.3                                                                             Cl                                        I-607 J-4   --      H    N   OCF.sub.2 H                                                                          OCF.sub.2 H                               I-608 J-4   --      H    N   OCF.sub.2 H                                                                          NHCH.sub.3                                I-609 J-4   --      H    N   OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-610 J-4   --      H    N   OCF.sub.2 H                                                                          Cl                                        I-611 J-4   --      H    N   NHCH.sub.3                                                                           NHCH.sub.3                                I-612 J-4   --      H    N   NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-613 J-4   --      H    N   NHCH.sub.3                                                                           Cl                                        I-614 J-4   --      H    N   N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-615 J-4   --      H    N   N(CH.sub.3).sub.2                                                                    Cl                                        I-616 J-4   --      H    N   Cl     Cl                                        I-617 J-4   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            OCH.sub.3                                                                            97-100.sup.(+)                     I-618 J-4   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            OC.sub.2 H.sub.5                          I-619 J-4   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            CH.sub.3                                  I-620 J-4   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            C.sub.2 H.sub.5                           I-621 J-4   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            CF.sub.3                                  I-622 J-4   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            OCF.sub.2 H                               I-623 J-4   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            NHCH.sub.3                                I-624 J-4   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            N(CH.sub.3).sub.2                         I-625 J-4   --      CH.sub.3                                                                           N   OCH.sub.3                                                                            Cl                                        I-626 J-4   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          I-627 J-4   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     CH.sub.3                                  I-628 J-4   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                           I-629 J-4   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     CF.sub.3                                  I-630 J-4   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                               I-631 J-4   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                I-632 J-4   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                         I-633 J-4   --      CH.sub.3                                                                           N   OC.sub.2 H.sub.5                                                                     Cl                                        I-634 J-4   --      CH.sub.3                                                                           N   CH.sub.3                                                                             CH.sub.3                                  I-635 J-4   --      CH.sub.3                                                                           N   CH.sub.3                                                                             C.sub.2 H.sub.5                           I-636 J-4   --      CH.sub.3                                                                           N   CH.sub.3                                                                             CF.sub.3                                  I-637 J-4   --      CH.sub.3                                                                           N   CH.sub.3                                                                             OCF.sub.2 H                               I-638 J-4   --      CH.sub.3                                                                           N   CH.sub.3                                                                             NHCH.sub.3                                I-639 J-4   --      CH.sub.3                                                                           N   CH.sub.3                                                                             N(CH.sub.3).sub.2                         I-640 J-4   --      CH.sub.3                                                                           N   CH.sub.3                                                                             Cl                                        I-641 J-4   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                           I-642 J-4   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      CF.sub.3                                  I-643 J-4   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      OCF.sub.2 H                               I-644 J-4   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      NHCH.sub.3                                I-645 J-4   --      CH.sub.3                                                                           N   C.sub.2 H.sub.5                                                                      Cl                                        I-646 J-4   --      CH.sub.3                                                                           N   CF.sub.3                                                                             CF.sub.3                                  I-647 J-4   --      CH.sub.3                                                                           N   CF.sub.3                                                                             OCF.sub.2 H                               I-648 J-4   --      CH.sub.3                                                                           N   CF.sub.3                                                                             NHCH.sub.3                                I-649 J-4   --      CH.sub.3                                                                           N   CF.sub.3                                                                             N(CH.sub.3).sub.2                         I-650 J-4   --      CH.sub.3                                                                           N   CF.sub.3                                                                             Cl                                        I-651 J-4   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          OCF.sub.2 H                               I-652 J-4   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          NHCH.sub.3                                I-653 J-4   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                         I-654 J-4   --      CH.sub.3                                                                           N   OCF.sub.2 H                                                                          Cl                                        I-655 J-4   --      CH.sub.3                                                                           N   NHCH.sub.3                                                                           NHCH.sub.3                                I-656 J-4   --      CH.sub.3                                                                           N   NHCH.sub.3                                                                           N(CH.sub.3).sub.2                         I-657 J-4   --      CH.sub.3                                                                           N   NHCH.sub.3                                                                           Cl                                        I-658 J-4   --      CH.sub.3                                                                           N   N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                         I-659 J-4   --      CH.sub.3                                                                           N   N(CH.sub.3).sub.2                                                                    Cl                                        I-660 J-4   --      CH.sub.3                                                                           N   Cl     Cl                                        ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                        Examples of compounds of the formula (I) having J = J-1;                      R.sup.4 = R.sup.5 = R.sup.6 = R.sup.7 = H and R.sup.10 = 6-CH.sub.3 :         Ex. No.                                                                             J      E      R.sup.1                                                                            A    R.sup.2                                                                              R.sup.3                                                                              m.p. (°C.)                 ______________________________________                                        I-661 J-1    --     H    CH   OCH.sub.3                                                                            OCH.sub.3                                I-662 J-1    --     H    CH   OCH.sub.3                                                                            OC.sub.2 H.sub.5                         I-663 J-1    --     H    CH   OCH.sub.3                                                                            CH.sub.3                                 I-664 J-1    --     H    CH   OCH.sub.3                                                                            C.sub.2 H.sub.5                          I-665 J-1    --     H    CH   OCH.sub.3                                                                            CF.sub.3                                 I-666 J-1    --     H    CH   OCH.sub.3                                                                            OCF.sub.2 H                              I-667 J-1    --     H    CH   OCH.sub.3                                                                            NHCH.sub.3                               I-668 J-1    --     H    CH   OCH.sub.3                                                                            N(CH.sub.3).sub.2                        I-669 J-1    --     H    CH   OCH.sub.3                                                                            Cl                                       I-670 J-1    --     H    CH   OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                         I-671 J-1    --     H    CH   OC.sub.2 H.sub.5                                                                     CH.sub.3                                 I-672 J-1    --     H    CH   OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                          I-673 J-1    --     H    CH   OC.sub.2 H.sub.5                                                                     CF.sub.3                                 I-674 J-1    --     H    CH   OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                              I-675 J-1    --     H    CH   OC.sub.2 H.sub.5                                                                     NHCH.sub.3                               I-676 J-1    --     H    CH   OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                        I-677 J-1    --     H    CH   OC.sub.2 H.sub.5                                                                     Cl                                       I-678 J-1    --     H    CH   CH.sub.3                                                                             CH.sub.3                                 I-679 J-1    --     H    CH   CH.sub.3                                                                             C.sub.2 H.sub.5                          I-680 J-1    --     H    CH   CH.sub.3                                                                             CF.sub.3                                 I-681 J-1    --     H    CH   CH.sub.3                                                                             OCF.sub.2 H                              I-682 J-1    --     H    CH   CH.sub.3                                                                             NHCH.sub.3                               I-683 J-1    --     H    CH   CH.sub.3                                                                             N(CH.sub.3).sub.2                        I-684 J-1    --     H    CH   CH.sub.3                                                                             Cl                                       I-685 J-1    --     H    CH   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                          I-686 J-1    --     H    CH   C.sub.2 H.sub.5                                                                      CF.sub.3                                 I-687 J-1    --     H    CH   C.sub.2 H.sub.5                                                                      OCF.sub.2 H                              I-688 J-1    --     H    CH   C.sub.2 H.sub.5                                                                      NHCH.sub.3                               I-689 J-1    --     H    CH   C.sub.2 H.sub.5                                                                      Cl                                       I-690 J-1    --     H    CH   CF.sub.3                                                                             CF.sub.3                                 I-691 J-1    --     H    CH   CF.sub.3                                                                             OCF.sub.2 H                              I-692 J-1    --     H    CH   CF.sub.3                                                                             NHCH.sub.3                               I-693 J-1    --     H    CH   CF.sub.3                                                                             N(CH.sub.3).sub.2                        I-694 J-1    --     H    CH   CF.sub.3                                                                             Cl                                       I-695 J-1    --     H    CH   OCF.sub.2 H                                                                          OCF.sub.2 H                              I-696 J-1    --     H    CH   OCF.sub.2 H                                                                          NHCH.sub.3                               I-697 J-1    --     H    CH   OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                        I-698 J-1    --     H    CH   OCF.sub.2 H                                                                          Cl                                       I-699 J-1    --     H    CH   NHCH.sub.3                                                                           NHCH.sub.3                               I-700 J-1    --     H    CH   NHCH.sub.3                                                                           N(CH.sub.3).sub.2                        I-701 J-1    --     H    CH   NHCH.sub.3                                                                           Cl                                       I-702 J-1    --     H    CH   N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                        I-703 J-1    --     H    CH   N(CH.sub.3).sub.2                                                                    Cl                                       I-704 J-1    --     H    CH   Cl     Cl                                       I-705 J-1    --     H    N    OCH.sub.3                                                                            OCH.sub.3                                I-706 J-1    --     H    N    OCH.sub.3                                                                            OC.sub.2 H.sub.5                         I-707 J-1    --     H    N    OCH.sub.3                                                                            CH.sub.3                                 I-708 J-1    --     H    N    OCH.sub.3                                                                            C.sub.2 H.sub.5                          I-709 J-1    --     H    N    OCH.sub.3                                                                            CF.sub.3                                 I-710 J-1    --     H    N    OCH.sub.3                                                                            OCF.sub.2 H                              I-711 J-1    --     H    N    OCH.sub.3                                                                            NHCH.sub.3                               I-712 J-1    --     H    N    OCH.sub.3                                                                            N(CH.sub.3).sub.2                        I-713 J-1    --     H    N    OCH.sub.3                                                                            Cl                                       I-714 J-1    --     H    N    OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                         I-715 J-1    --     H    N    OC.sub.2 H.sub.5                                                                     CH.sub.3                                 I-716 J-1    --     H    N    OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                          I-717 J-1    --     H    N    OC.sub.2 H.sub.5                                                                     CF.sub.3                                 I-718 J-1    --     H    N    OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                              I-719 J-1    --     H    N    OC.sub.2 H.sub.5                                                                     NHCH.sub.3                               I-720 J-1    --     H    N    OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                        I-721 J-1    --     H    N    OC.sub.2 H.sub.5                                                                     Cl                                       I-722 J-1    --     H    N    CH.sub.3                                                                             CH.sub.3                                 I-723 J-1    --     H    N    CH.sub.3                                                                             C.sub.2 H.sub.5                          I-724 J-1    --     H    N    CH.sub.3                                                                             CF.sub.3                                 I-725 J-1    --     H    N    CH.sub.3                                                                             OCF.sub.2 H                              I-726 J-1    --     H    N    CH.sub.3                                                                             NHCH.sub.3                               I-727 J-1    --     H    N    CH.sub.3                                                                             N(CH.sub.3).sub.2                        I-728 J-1    --     H    N    CH.sub.3                                                                             Cl                                       I-729 J-1    --     H    N    C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                          I-730 J-1    --     H    N    C.sub.2 H.sub.5                                                                      CF.sub.3                                 I-731 J-1    --     H    N    C.sub.2 H.sub.5                                                                      OCF.sub.2 H                              I-732 J-1    --     H    N    C.sub.2 H.sub.5                                                                      NHCH.sub.3                               I-733 J-1    --     H    N    C.sub.2 H.sub.5                                                                      Cl                                       I-734 J-1    --     H    N    CF.sub.3                                                                             CF.sub.3                                 I-335 J-1    --     H    N    CF.sub.3                                                                             OCF.sub.2 H                              I-736 J-1    --     H    N    CF.sub.3                                                                             NHCH.sub.3                               I-737 J-1    --     H    N    CF.sub.3                                                                             N(CH.sub.3).sub.2                        I-738 J-1    --     H    N    CF.sub.3                                                                             Cl                                       I-739 J-1    --     H    N    OCF.sub.2 H                                                                          OCF.sub.2 H                              I-740 J-1    --     H    N    OCF.sub.2 H                                                                          NHCH.sub.3                               I-741 J-1    --     H    N    OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                        I-742 J-1    --     H    N    OCF.sub.2 H                                                                          Cl                                       I-743 J-1    --     H    N    NHCH.sub.3                                                                           NHCH.sub.3                               I-744 J-1    --     H    N    NHCH.sub.3                                                                           N(CH.sub.3).sub.2                        I-745 J-1    --     H    N    NHCH.sub.3                                                                           Cl                                       I-746 J-1    --     H    N    N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                        I-747 J-1    --     H    N    N(CH.sub.3).sub.2                                                                    Cl                                       I-748 J-1    --     H    N    Cl     Cl                                       I-749 J-1    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            OCH.sub.3                                I-750 J-1    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            OC.sub.2 H.sub.5                         I-751 J-1    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            CH.sub.3                                 I-752 J-1    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            C.sub.2 H.sub.5                          I-753 J-1    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            CF.sub.3                                 I-754 J-1    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            OCF.sub.2 H                              I-755 J-1    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            NHCH.sub.3                               I-756 J-1    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            N(CH.sub.3).sub.2                        I-757 J-1    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            Cl                                       I-758 J-1    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                         I-759 J-1    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     CH.sub.3                                 I-760 J-1    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                          I-761 J-1    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     CF.sub.3                                 I-762 J-1    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                              I-763 J-1    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     NHCH.sub.3                               I-764 J-1    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                        I-765 J-1    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     Cl                                       I-766 J-1    --     CH.sub.3                                                                           N    CH.sub.3                                                                             CH.sub.3                                 I-767 J-1    --     CH.sub.3                                                                           N    CH.sub.3                                                                             C.sub.2 H.sub.5                          I-768 J-1    --     CH.sub.3                                                                           N    CH.sub.3                                                                             CF.sub.3                                 I-769 J-1    --     CH.sub.3                                                                           N    CH.sub.3                                                                             OCF.sub.2 H                              I-770 J-1    --     CH.sub.3                                                                           N    CH.sub.3                                                                             NHCH.sub.3                               I-771 J-1    --     CH.sub.3                                                                           N    CH.sub.3                                                                             N(CH.sub.3).sub.2                        I-772 J-1    --     CH.sub.3                                                                           N    CH.sub.3                                                                             Cl                                       I-773 J-1    --     CH.sub.3                                                                           N    C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                          I-774 J-1    --     CH.sub.3                                                                           N    C.sub.2 H.sub.5                                                                      CF.sub.3                                 I-775 J-1    --     CH.sub.3                                                                           N    C.sub.2 H.sub.5                                                                      OCF.sub.2 H                              I-776 J-1    --     CH.sub.3                                                                           N    C.sub.2 H.sub.5                                                                      NHCH.sub.3                               I-777 J-1    --     CH.sub.3                                                                           N    C.sub.2 H.sub.5                                                                      Cl                                       I-778 J-1    --     CH.sub.3                                                                           N    CF.sub.3                                                                             CF.sub.3                                 I-779 J-1    --     CH.sub.3                                                                           N    CF.sub.3                                                                             OCF.sub.2 H                              I-780 J-1    --     CH.sub.3                                                                           N    CF.sub.3                                                                             NHCH.sub.3                               I-781 J-1    --     CH.sub.3                                                                           N    CF.sub.3                                                                             N(CH.sub.3).sub.2                        I-782 J-1    --     CH.sub.3                                                                           N    CF.sub.3                                                                             Cl                                       I-783 J-1    --     CH.sub.3                                                                           N    OCF.sub.2 H                                                                          OCF.sub.2 H                              I-784 J-1    --     CH.sub.3                                                                           N    OCF.sub.2 H                                                                          NHCH.sub.3                               I-785 J-1    --     CH.sub.3                                                                           N    OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                        I-786 J-1    --     CH.sub.3                                                                           N    OCF.sub.2 H                                                                          Cl                                       I-787 J-1    --     CH.sub.3                                                                           N    NHCH.sub.3                                                                           NHCH.sub.3                               I-788 J-1    --     CH.sub.3                                                                           N    NHCH.sub.3                                                                           N(CH.sub.3).sub.2                        I-789 J-1    --     CH.sub.3                                                                           N    NHCH.sub.3                                                                           Cl                                       I-790 J-1    --     CH.sub.3                                                                           N    N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                        I-791 J-1    --     CH.sub.3                                                                           N    N(CH.sub.3).sub.2                                                                    Cl                                       I-792 J-1    --     CH.sub.3                                                                           N    Cl     Cl                                       ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                        Examples of compounds of the formula (I) having J = J-3;                      R.sup.4 = R.sup.5 = R.sup.6 = R.sup.7 = H; R.sup.8 = CH.sub.3 and             R.sup.10 = Cl:                                                                Ex. No.                                                                             J      E      R.sup.1                                                                            A    R.sup.2                                                                              R.sup.3                                                                              m.p. (°C.)                 ______________________________________                                        I-793 J-3    --     H    CH   OCH.sub.3                                                                            OCH.sub.3                                                                            243.sup.(+)                       I-794 J-3    --     H    CH   OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                     117-120                                                                       187-190.sup.(+)                   I-795 J-3    --     H    CH   OCH.sub.3                                                                            CH.sub.3                                                                             188-194                                                                       214.sup.(+)                       I-796 J-3    --     H    CH   OCH.sub.3                                                                            C.sub.2 H.sub.5                          I-797 J-3    --     H    CH   OCH.sub.3                                                                            CF.sub.3                                 I-798 J-3    --     H    CH   OCH.sub.3                                                                            OCF.sub.2 H                              I-799 J-3    --     H    CH   OCH.sub.3                                                                            NHCH.sub.3                               I-800 J-3    --     H    CH   OCH.sub.3                                                                            N(CH.sub.3).sub.2                        I-801 J-3    --     H    CH   OCH.sub.3                                                                            Cl     177-178                                                                       200-201.sup.(+)                   I-802 J-3    --     H    CH   OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                     187-193                           I-803 J-3    --     H    CH   OC.sub.2 H.sub.5                                                                     CH.sub.3                                 I-804 J-3    --     H    CH   OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                          I-805 J-3    --     H    CH   OC.sub.2 H.sub.5                                                                     CF.sub.3                                 I-806 J-3    --     H    CH   OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                              I-807 J-3    --     H    CH   OC.sub.2 H.sub.5                                                                     NHCH.sub.3                               I-808 J-3    --     H    CH   OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                        I-809 J-3    --     H    CH   OC.sub.2 H.sub.5                                                                     Cl     173-175                                                                       218.sup.(+)                       I-810 J-3    --     H    CH   CH.sub.3                                                                             CH.sub.3                                                                             193-194                                                                       228-230.sup.(+)                   I-811 J-3    --     H    CH   CH.sub.3                                                                             C.sub.2 H.sub.5                          I-812 J-3    --     H    CH   CH.sub.3                                                                             CF.sub.3                                 I-813 J-3    --     H    CH   CH.sub.3                                                                             OCF.sub.2 H                              I-814 J-3    --     H    CH   CH.sub.3                                                                             NHCH.sub.3                               I-815 J-3    --     H    CH   CH.sub.3                                                                             N(CH.sub.3).sub.2                        I-816 J-3    --     H    CH   CH.sub.3                                                                             Cl     190                                                                           205.sup.(+)                       I-817 J-3    --     H    CH   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                          I-818 J-3    --     H    CH   C.sub.2 H.sub.5                                                                      CF.sub.3                                 I-819 J-3    --     H    CH   C.sub.2 H.sub.5                                                                      OCF.sub.2 H                              I-820 J-3    --     H    CH   C.sub.2 H.sub.5                                                                      NHCH.sub.3                               I-821 J-3    --     H    CH   C.sub.2 H.sub.5                                                                      Cl                                       I-822 J-3    --     H    CH   CF.sub.3                                                                             CF.sub.3                                 I-823 J-3    --     H    CH   CF.sub.3                                                                             OCF.sub.2 H                              I-824 J-3    --     H    CH   CF.sub.3                                                                             NHCH.sub.3                               I-825 J-3    --     H    CH   CF.sub.3                                                                             N(CH.sub.3).sub.2                        I-826 J-3    --     H    CH   CF.sub.3                                                                             Cl                                       I-827 J-3    --     H    CH   OCF.sub.2 H                                                                          OCF.sub.2 H                              I-828 J-3    --     H    CH   OCF.sub.2 H                                                                          NHCH.sub.3                               I-829 J-3    --     H    CH   OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                        I-830 J-3    --     H    CH   OCF.sub.2 H                                                                          Cl                                       I-831 J-3    --     H    CH   NHCH.sub.3                                                                           NHCH.sub.3                               I-832 J-3    --     H    CH   NHCH.sub.3                                                                           N(CH.sub.3).sub.2                        I-833 J-3    --     H    CH   NHCH.sub.3                                                                           Cl                                       I-834 J-3    --     H    CH   N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                        I-835 J-3    --     H    CH   N(CH.sub.3).sub.2                                                                    Cl                                       I-836 J-3    --     H    CH   Cl     Cl                                       I-837 J-3    --     H    N    OCH.sub.3                                                                            OCH.sub.3                                                                            172                                                                           218.sup.(+)                       I-838 J-3    --     H    N    OCH.sub.3                                                                            OC.sub.2 H.sub.5                         I-839 J-3    --     H    N    OCH.sub.3                                                                            CH.sub.3                                                                             190-192.sup.(+)                   I-840 J-3    --     H    N    OCH.sub.3                                                                            C.sub.2 H.sub.5                          I-841 J-3    --     H    N    OCH.sub.3                                                                            CF.sub.3                                 I-842 J-3    --     H    N    OCH.sub.3                                                                            OCF.sub.2 H                              I-843 J-3    --     H    N    OCH.sub.3                                                                            NHCH.sub.3                               I-844 J-3    --     H    N    OCH.sub.3                                                                            N(CH.sub.3).sub.2                        I-845 J-3    --     H    N    OCH.sub.3                                                                            Cl                                       I-846 J-3    --     H    N    OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                         I-847 J-3    --     H    N    OC.sub.2 H.sub.5                                                                     CH.sub.3                                 I-848 J-3    --     H    N    OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                          I-849 J-3    --     H    N    OC.sub.2 H.sub.5                                                                     CF.sub.3                                 I-850 J-3    --     H    N    OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                              I-851 J-3    --     H    N    OC.sub.2 H.sub.5                                                                     NHCH.sub.3                               I-852 J-3    --     H    N    OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                        I-853 J-3    --     H    N    OC.sub.2 H.sub.5                                                                     Cl                                       I-854 J-3    --     H    N    CH.sub.3                                                                             CH.sub.3                                                                             151-153                                                                       130-135.sup.(+)                   I-855 J-3    --     H    N    CH.sub.3                                                                             C.sub.2 H.sub.5                          I-856 J-3    --     H    N    CH.sub.3                                                                             CF.sub.3                                 I-857 J-3    --     H    N    CH.sub.3                                                                             OCF.sub.2 H                              I-858 J-3    --     H    N    CH.sub.3                                                                             NHCH.sub.3                               I-859 J-3    --     H    N    CH.sub.3                                                                             N(CH.sub.3).sub.2                        I-860 J-3    --     H    N    CH.sub.3                                                                             Cl                                       I-861 J-3    --     H    N    C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                          I-862 J-3    --     H    N    C.sub.2 H.sub.5                                                                      CF.sub.3                                 I-863 J-3    --     H    N    C.sub.2 H.sub.5                                                                      OCF.sub.2 H                              I-864 J-3    --     H    N    C.sub.2 H.sub.5                                                                      NHCH.sub.3                               I-865 J-3    --     H    N    C.sub.2 H.sub.5                                                                      Cl                                       I-866 J-3    --     H    N    CF.sub.3                                                                             CF.sub.3                                 I-867 J-3    --     H    N    CF.sub.3                                                                             OCF.sub.2 H                              I-868 J-3    --     H    N    CF.sub.3                                                                             NHCH.sub.3                               I-869 J-3    --     H    N    CF.sub.3                                                                             N(CH.sub.3).sub.2                        I-870 J-3    --     H    N    CF.sub.3                                                                             Cl                                       I-871 J-3    --     H    N    OCF.sub.2 H                                                                          OCF.sub.2 H                              I-872 J-3    --     H    N    OCF.sub.2 H                                                                          NHCH.sub.3                               I-873 J-3    --     H    N    OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                        I-874 J-3    --     H    N    OCF.sub.2 H                                                                          Cl                                       I-875 J-3    --     H    N    NHCH.sub.3                                                                           NHCH.sub.3                               I-876 J-3    --     H    N    NHCH.sub.3                                                                           N(CH.sub.3).sub.2                        I-877 J-3    --     H    N    NHCH.sub.3                                                                           Cl                                       I-878 J-3    --     H    N    N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                        I-879 J-3    --     H    N    N(CH.sub.3).sub.2                                                                    Cl                                       I-880 J-3    --     H    N    Cl     Cl                                       I-881 J-3    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            OCH.sub.3                                                                            172-173                                                                       110-114.sup.(+)                   I-882 J-3    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            OC.sub.2 H.sub.5                         I-883 J-3    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            CH.sub.3                                 I-884 J-3    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            C.sub.2 H.sub.5                          I-885 J-3    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            CF.sub.3                                 I-886 J-3    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            OCF.sub.2 H                              I-887 J-3    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            NHCH.sub.3                               I-888 J-3    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            N(CH.sub.3).sub.2                        I-889 J-3    --     CH.sub.3                                                                           N    OCH.sub.3                                                                            Cl                                       I-890 J-3    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                         I-891 J-3    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     CH.sub.3                                 I-892 J-3    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                          I-893 J-3    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     CF.sub.3                                 I-894 J-3    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     OCF.sub.2 H                              I-895 J-3    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     NHCH.sub.3                               I-896 J-3    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     N(CH.sub.3).sub.2                        I-897 J-3    --     CH.sub.3                                                                           N    OC.sub.2 H.sub.5                                                                     Cl                                       I-898 J-3    --     CH.sub.3                                                                           N    CH.sub.3                                                                             CH.sub.3                                 I-899 J-3    --     CH.sub.3                                                                           N    CH.sub.3                                                                             C.sub.2 H.sub.5                          I-900 J-3    --     CH.sub.3                                                                           N    CH.sub.3                                                                             CF.sub.3                                 I-901 J-3    --     CH.sub.3                                                                           N    CH.sub.3                                                                             OCF.sub.2 H                              I-902 J-3    --     CH.sub.3                                                                           N    CH.sub.3                                                                             NHCH.sub.3                               I-903 J-3    --     CH.sub.3                                                                           N    CH.sub.3                                                                             N(CH.sub.3).sub.2                        I-904 J-3    --     CH.sub.3                                                                           N    CH.sub.3                                                                             Cl                                       I-905 J-3    --     CH.sub.3                                                                           N    C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                          I-906 J-3    --     CH.sub.3                                                                           N    C.sub.2 H.sub.5                                                                      CF.sub.3                                 I-907 J-3    --     CH.sub.3                                                                           N    C.sub.2 H.sub.5                                                                      OCF.sub.2 H                              I-908 J-3    --     CH.sub.3                                                                           N    C.sub.2 H.sub.5                                                                      NHCH.sub.3                               I-909 J-3    --     CH.sub.3                                                                           N    C.sub.2 H.sub.5                                                                      Cl                                       I-910 J-3    --     CH.sub.3                                                                           N    CF.sub.3                                                                             CF.sub.3                                 I-911 J-3    --     CH.sub.3                                                                           N    CF.sub.3                                                                             OCF.sub.2 H                              I-912 J-3    --     CH.sub.3                                                                           N    CF.sub.3                                                                             NHCH.sub.3                               I-913 J-3    --     CH.sub.3                                                                           N    CF.sub.3                                                                             N(CH.sub.3).sub.2                        I-914 J-3    --     CH.sub.3                                                                           N    CF.sub.3                                                                             Cl                                       I-915 J-3    --     CH.sub.3                                                                           N    OCF.sub.2 H                                                                          OCF.sub.2 H                              I-916 J-3    --     CH.sub.3                                                                           N    OCF.sub.2 H                                                                          NHCH.sub.3                               I-917 J-3    --     CH.sub.3                                                                           N    OCF.sub.2 H                                                                          N(CH.sub.3).sub.2                        I-918 J-3    --     CH.sub.3                                                                           N    OCF.sub.2 H                                                                          Cl                                       I-919 J-3    --     CH.sub.3                                                                           N    NHCH.sub.3                                                                           NHCH.sub.3                               I-920 J-3    --     CH.sub.3                                                                           N    NHCH.sub.3                                                                           N(CH.sub.3).sub.2                        I-921 J-3    --     CH.sub.3                                                                           N    NHCH.sub.3                                                                           Cl                                       I-922 J-3    --     CH.sub.3                                                                           N    N(CH.sub.3).sub.2                                                                    N(CH.sub.3).sub.2                        I-923 J-3    --     CH.sub.3                                                                           N    N(CH.sub.3).sub.2                                                                    Cl                                       I-924 J-3    --     CH.sub.3                                                                           N    Cl     Cl                                       ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                        Examples of compounds of the formula (I) having                               R.sup.1 = R.sup.4 = R.sup.5 = R.sup.6 = R.sup.7 = R.sup.10 = H                Ex. No.                                                                             J      E      R.sup.1                                                                            A      R.sup.2                                                                              R.sup.3                                                                            m.p. (°C.)                 ______________________________________                                        I-925                                                                              J-1    --     CH   OC.sub.6 H.sub.5                                                                      CH.sub.3                                                                             --   105-109                                                                       186-190.sup.(+)                   I-926                                                                              J-1    --     CH   Cl      OCH.sub.2 CF.sub.3                                                                   --   111                                                                           120-124.sup.(+)                   I-927                                                                              J-2    --     N    N(CH.sub.3).sub.2                                                                     OCH.sub.2 CF.sub.3                                                                   --   158                               I-928                                                                              J-2    --     CH   Cl      OCH.sub.2 CF.sub.3                                                                   --   204-205                                                                       207.sup.(+)                       I-929                                                                              J-3    --     CH   Cl      OCH.sub.2 CF.sub.3                                                                   CH.sub.3                                                                           110                                                                           214-218.sup.(+)                   I-930                                                                              J-3    --     N    N(CH.sub.3).sub.2                                                                     OCH.sub.2 CF.sub.3                                                                   CH.sub.3                                                                           183-184                                                                       214-216.sup.(+)                   I-931                                                                              J-3    --     CH   CH.sub.3                                                                              OC.sub.6 H.sub.5                                                                     CH.sub.3                                                                           195-198                                                                       248-249.sup.(+)                   I-932                                                                              J-4    --     CH   Cl      OCH.sub.2 CF.sub.3                                                                   --   115-118                                                                       166.sup.(+)                       I-933                                                                              J-4    --     N    N(CH.sub.3).sub.2                                                                     OCH.sub.2 CF.sub.3                                                                   --   173-174                           I-934                                                                              J-4    --     CH   CH.sub.3                                                                              OC.sub.6 H.sub.5                                                                     --   104-108                                                                       184.sup.(+)                       ______________________________________                                    

Salts of compounds of the formula (I)

Example I-397-a ##STR20##

0.5 g (0.01 mol) of 80% sodium hydroxide powder are added, whilststirring, to a mixture consisting of 4.3 g (0.01 mol) ofN-(4,6-dimethoxypyrimidin-2-yl)-N'-(1-methyl-4-(5,6-dihydro-1,4,2!-dioxazin-3-yl)pyrazole-5-sulphonyl)-urea and 100 ml of toluene.The mixture is stirred at 20° C. for 15 hours; the crystalline productis subsequently isolated by filtering off with suction.

4.5 g (99% of theory) ofN-(4,6-dimethoxypyrimidin-2-yl)-N'-(1-methyl-4-(5,6-dihydro-1,4,2!-dioxazin-3-yl)pyrazole-5-sulphonyl)-urea Na salt are obtainedwith a melting point of 250° C. (with decomposition).

The following are obtained in an analogous manner:

Example I-89-a ##STR21##

N-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-N-methyl-N'-(2-(5,6-dihydro-1,4,2!-dioxazin-3-yl)benzenesulphonyl)-urea Na salt.

Melting point 146°-149° C.

Example I-617-a ##STR22##

N-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-N-methyl-N'-(2-(5,6-dihydro-1,4,2!-dioxazin-3-yl)-thiophene-3-sulphonyl)-urea Na salt.

Melting point 97°-100° C.

Starting compounds of the formula (II)

Example (II-1) ##STR23## (Process (d))

Chlorine is passed, at 0° C., into a mixture consisting of 22.7 g(0.0795 mol) of 1-benzylthio-2-(5,6-dihydro-1,4,2!-dioxazin-3-yl)-benzene in 150 ml of dichloromethane and 70 g ofsodium dihydrogen phosphate hydrate in 150 ml of water until it issaturated. Subsequently, the phases are separated, the organic phase isdried, and the solvent is stripped off under reduced pressure. Thesulphonyl chloride which is formed under these circumstances is taken upin 50 ml of absolute tetrahydrofuran and this solution is added dropwiseat -40° C. to a mixture consisting of 500 ml of tetrahydrofuran and 50ml of ammonia. Stirring of the mixture is continued at room temperaturefor a further 2 hours and the precipitated salts are then filtered offwith suction. The filtrate is freed from the solvent under reducedpressure and the residue is chromatographed (eluents: 1.dichloromethane, 2. cyclohexane/ethyl acetate 1:1). 11.5 g (60% oftheory) of 2-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)-benzenesulphonamide areobtained as a pale yellow solid.

Melting point: 131°-133° C.

The following are obtained in an analogous manner:

Example II-2 ##STR24##

2-(5,6-Dihydro- 1,4,2!-dioxazin-3-yl)phenylmethanesulphonamide.

Melting point: . . . °C.

Example II-3 ##STR25##

3-(5,6-Dihydro- 1,4,2!-dioxazin-3-yl)-pyridine-2-sulphonamide.

Melting point: 170° C.

Example II-4

(Process (e)) ##STR26##

6.28 g (0.112 mol) of potassium hydroxide in 100 ml of methanol areadded dropwise, at room temperature, to a mixture of 7.78 g (0.112 mol)of hydroxylamine hydrochloride and 150 ml of methanol. Subsequently,13.1 g (0.056 mol) of 1-methyl-5-ethoxycarbonylpyrazole-4-sulphonamideare added in portions at room temperature. The mixture is stirred atroom temperature overnight, and subsequently at 40° C. for 2 hours andat 60° C. for a further 2 hours. 3.14 g (0.056 mol) of potassiumhydroxide in 50 ml of methanol are added dropwise, and the mixture isthen stirred at 60° C. for a further 2 hours. 7.74 g (0.056 mol) ofpotassium carbonate are then added, 50.5 g (0.25 mol) of1,2-dibromoethane (BrCH₂ CH₂ Br) are added dropwise, and the mixture issubsequently left stirring at 60° C. overnight. Subsequently, thesolvent is distilled off under reduced pressure. The residue ispartitioned between methylene chloride and water. The organic phase isdried and the solvent is distilled off under reduced pressure. Theresidue is chromatographed (eluent: cyclohexane/ethyl acetate 2:3).

5.91 g (43% of theory) of 1-methyl-5-(5,6-dihydro-1,4,2!-dioxazin-3-yl)pyrazole-4-sulphonamide are obtained as a paleyellow solid.

Melting point: 126°-130° C.

The following is obtained in an analogous manner:

Example II-5 ##STR27##

2-(5,6-Dihydro- 1,4,2!-dioxazin-3-yl)thiophene-3-sulphonamide.

Melting point: 180°-184° C.

Starting compounds of the formula (VII)

Example (VII-1) ##STR28##

160 g (2.86 mol) of potassium hydroxide in 700 ml of methanol are addeddropwise, at room temperature, to a mixture of 98.7 g (1.42 mol) ofhydroxylamine hydrochloride and 700 ml of methanol. Subsequently, 184 g(0.712 mol) of methyl 2-(benzylthio)benzoate are added in portions atroom temperature. The mixture is stirred at 40° C. overnight. 98.1 g(0.712 mol) of potassium carbonate are then added, 601 g (3.20 mol) of1,2-dibromoethane are added dropwise, and the mixture is left stirringat 60° C. overnight. Subsequently, the solvent is distilled off underreduced pressure. The residue is partitioned between methylene chlorideand water. The organic phase is dried and the solvent is distilled offunder reduced pressure. The residue is stirred up with absolute ethylalcohol. The solid is filtered off with suction and dried under highvacuum.

43.1 g (21% of theory) of 1-benzylthio-2-(5,6-dihydro-1,4,2!-dioxazin-3-yl)benzene are obtained as a pale yellow solid.

Melting point: 73°-77° C.

The following is obtained in an analogous manner:

Example VII-2 ##STR29##

2-Benzylthio-3-(5,6-dihydro- 1,4,2!-dioxazin-3-yl)pyridine.

Melting point: 65°-67.5° C.

Application Examples

In the following application examples, the compounds listed below aretaken as compounds for comparison: ##STR30##

N-(4,6-Dimethylpyrimidin-2-yl)-N'-(2-methoxyaminocarbonyl-phenylsulphonyl)-urea;and ##STR31##

N-(4,6-dimethylpyrimidin-2-yl)-N'-(2-n-octyloxyaminocarbonyl-phenylsulphonyl)-urea,

(both known from DE-A-3 516 435, Examples 1 and 2, respectively).

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours,watered with the preparation of the active compound. It is expedient tokeep constant the amount of water per unit area. The concentration ofthe active compound in the preparation is of no importance, only theamount of active compound applied per unit area being decisive. Afterthree weeks, the degree of damage to the plants is rated in % damage incomparison to the development of the untreated control. The figuresdenote:

0%=no action (like untreated control)

100%=total destruction

A clear superiority in activity as compared with the state of the art isshown in this test by, for example, the compounds according to thefollowing preparation examples: (I-1), (I-9), (I-18), (I-47).

Example B

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is so chosen that the particularamounts of active compound desired are applied in 2,000 l of water/ha.After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

0%=no action (like untreated control)

100%=total destruction

A clear superiority in activity as compared with the state of the art isshown in this test by, for example, the compounds according to thefollowing preparation examples: (I-1), (I-18), (I-47), (I-89a), (I-397),(I-414), (I-485).

It will be appreciated that the instant specification and claims are setforth by way of illustration and not limitation, and that variousmodifications and changes may be made without departing from the spiritand scope of the present invention.

We claim:
 1. A (het)arylsulphonyl compound of the formula

    J--SO.sub.2 --G

wherein G is --NH₂, N═C═O or --NH--COOR¹² wherein R¹² is alkyl or aryl,J is a member selected from the group consisting of ##STR32## wherein Eis a direct linkage, alkylene, oxygen, alkylamino, or sulphur, R⁴, R⁵,R⁶ and R⁷ each is hydrogen, cyano or thiocyanato, or is alkyl, alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkylcarbonyl,alkoxycarbonyl or alkylaminocarbonyl having in each alkyl group 1 to 3carbon atoms optionally substituted by halogen, R⁸ is hydrogen, or anradical selected from the group consisting of alkyl, alkenyl, alkinyl,cycloalkyl, cycloalkylalkyl, aralkyl and aryl, or is C(═O)R⁹, R⁹ ishydrogen or alkyl, aryl, alkoxy, alkylamino or dialkylamino, and R¹⁰ ishydrogen, halogen, cyano or thiocyanato, or is alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, alkylcarbonyl,alkoxycarbonyl or alkylaminocarbonyl having in each alkyl group 1 to 3carbon atoms optionally substituted by halogen,wherein, unless otherwisespecified, the alkyl, alkylene, alkenyl and alkinyl groups have up to 6carbon atoms, the cycloalkyl groups 3 to 6 carbon atoms and the arylgroups 6 to 10 atoms.